To carry out our procedure, it needs to mix 1 mol each of sodium amide and choline chloride
![](data:image/png;base64,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)
Table 1 Screening of the reaction
|
Entry
|
Solvent
|
Time
|
Temperature
|
Yield *
|
1
|
Ch.Cl+ dry MeOH 1 : 2
|
overnight
|
65
|
28% B
|
2
|
Ch.Cl+dryTHF
|
overnight
|
75
|
23% B
|
3
|
Ch.Cl
|
overnight
|
40
|
23%A
|
4
|
Ch.Cl
|
overnight
|
25
|
TraceA
|
5
|
Ch.Cl
|
overnight
|
60
|
88% A
|
6
|
Ch.Cl
|
overnight
|
80
|
52%A,C
|
7
|
Ch.Cl+Urea
|
overnight
|
80
|
TraceB
|
8
|
Ch.Cl+thio-urea1 : 2
|
overnight
|
80
|
TraceB
|
9
|
Ch.Cl+ Ethylene glycol 1 : 2
|
overnight
|
60
|
TraceB
|
10
|
ChCl/boric acid 1 : 1.5
|
overnight
|
60
|
TraceB
|
11
|
Ch.Cl+ dry glycerol 1 : 2
|
overnight
|
80
|
TraceB
|
1mol choline chloride and 1mol Sodium amide were stirred for 45 minutes, then 1mol benzyl halides were added *Isolated Yield A: Inert atmosphere B: Air C: the reaction needs fractional distillation
|
for 45 minutes at 60 oC in an inert environment, then add 1 mol of benzyl chloride to the flask and let the reaction run overnight in the same manner (Table1-entry5) as a free solvent method. It is repeated in the proximity of solvents, but sodium amide, which reacts with moisture and solvents, is severely reactive (Table 1, entries 1 and 2). A novel method for producing benzylamine without producing salt by-products has been revealed. According to many investigations, the ideal reaction temperature is 60 °C (Table 1, entries 3-6). However, Deep eutectic solvent systems are also being studied as an alternative system. This system is a failure to produce benzylamine (Table 1, entries 7–10). aryl bromide & aryl chloride are being used in our experiments to evaluate how universal this approach is. Choline chloride/NH2 was used to react with aryl halides having electron-rich and electron-deficient units (1:1). These findings (table 2, 4a, -4i) reveal that the benzylamine yields ranged from fair to extraordinary. The production of benzylamine is simplified in this article thanks to a very efficient method described therein. Benzylamines are produced with outstanding yields, as demonstrated in Table 2. (Table 2, entries 4a,-4i).
![](data:image/png;base64,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)
Table 2 Screening of the derivatives reaction
Entry
|
R
|
Yield
Of Chloride
|
Yield
Of Bromide
|
Color
|
M.P.(°C)
|
Ref
|
4a,
|
H
|
77%
|
88%
|
yellow
|
liquid
|
-
|
4b,
|
4-NO2
|
78%
|
86%
|
yellow
|
39-40
|
-1
|
4c,
|
4-F
|
71%
|
82%
|
Colorless
|
liquid
|
|
4d,
|
2-Cl
|
75%
|
89%
|
Colorless
|
liquid
|
-
|
4e,
|
4-Cl
|
-
|
90%
|
Colorless
|
liquid
|
|
4f,
|
2,4-Cl
|
88%
|
-
|
yellow
|
liquid
|
-
|
4g,
|
4-Br
|
89%
|
89%
|
yellow
|
25
|
2
|
4h,
|
4-Me
|
84%
|
84%
|
Colorless
|
liquid
|
-
|
4i,
|
3-OMe
|
85%
|
88%
|
colourless
|
liquid
|
-
|
As part of our ongoing interest in creating novel techniques for synthesizing heterocyclic compounds34-36 utilizing eco chemistry, ionic liquids, and DESs9,37-38this paper also offers an extremely fast methodology for the synthesis of 1,2,3- triazoles and benzyl azides using a one-pot, three-component reactions in a choline chloride, as well as urea-based DES around 85 °C without employing a metal acid Lewis catalysts or organic solvents.
To carry out our procedure, it needs to mix 1 mol of sodium azide and choline chloride for 45 minutes at 60 oC, then add 1 mol of benzyl halides (1a) to the flask and let the reaction run for 2 hours and 15 minutes. Then urea and sodium acetate are added for two hours in the air condition, then aromatic aldehyde 3a plus nitro-methane are added. The response was carried out at 85OC, as a robust system is presented. The other conditions were probed (entries 3 and 8-11). It was discovered that the optimized reaction temp was 85OC (Table 3, entry 1). It was discovered that choline chloride is superior to the other cholines in terms of technical and economic performance (Table 3, items 4-7 and 1). That choline chloride is the most cost-effective and environmentally friendly media. In addition, the model reaction was used to test for the presence of different hydrogen bond donors. There were no effective results without urea, and the reaction yielded a modest amount of product with thiourea and ethylene glycol (Entries 2, 3, 11, and 12 in Table 3).
![](data:image/png;base64,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)
Table 3 Screening of the reaction four-component tandem assisted
|
Entry
|
HBA
|
HBD+Base
|
Temperature
|
Time
|
4a (%)
Yield
|
1
|
Ch.Cl
|
Urea 2mmol+1mmol NaOAC
|
85 OC
|
9.30h
|
89%
|
2
|
Ch.Cl
|
Thio-urea
|
85 OC
|
9.30h
|
51%
|
3
|
Ch. Cl
|
-
|
85 OC
|
9.30h
|
-
|
4
|
Ch.OH
|
Urea*2mmol
|
85 OC
|
9.30h
|
trace
|
5
|
Ch.OAc
|
Urea*2mmol
|
85 OC
|
9.30h
|
59%
|
6
|
Ch.HCO3
|
Urea*2mmol
|
85 OC
|
9.30h
|
25%
|
7
|
Ch2.HPO3
|
Urea*2mmol
|
85 OC
|
9.30h
|
24%
|
8
|
Ch.Cl
|
Urea 2mmol+1mmol NaOAC
|
25 OC
|
9.30h
|
-
|
9
|
Ch.Cl
|
Urea 2mmol+1mmol NaOAC
|
40 OC
|
9.30h
|
15%
|
10
|
Ch.Cl
|
Urea 2mmol+1mmol NaOAC
|
60 OC
|
9.30h
|
36%
|
11
|
Ch. Cl
|
glycerol
|
60 OC
|
9.30h
|
59%
|
12
|
Ch.Cl
|
Ethylene glycol
|
60 OC
|
9.30h
|
57%
|
Following the optimization of the circumstances, we aimed to determine the range of halides and aldehydes that were receptive to cycloaddition (Table 4). Aromatic halides and aldehydes, primarily cheap and readily available, were excellent substrates for producing 1,2,3-triazoles in high yield. It has been demonstrated that nitro styrenes and an array of substituted benzyl halides bearing both electron-donating and electron-withdrawing functions may effectively interact to yield 1,2,3- triazoles. It was discovered that aldehydes and halides might produce the necessary products in yields ranging from 64-89% under inadequate reaction conditions (table 4, 4a-4k). The proposed mechanism can be found with more details in supporting information.
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)
Table 4 Screening of the derivatives reaction
|
Product 4
|
R1
|
R2
|
Yield (%)
|
M.P.(°C)
|
Ref
|
a
|
H
|
H
|
89%
|
131-133
|
39
|
b
|
4OMe
|
H
|
87%
|
117-119ᵒC
|
3
|
c
|
4NO2
|
H
|
71%
|
140-141
|
4
|
d
|
H
|
3-Me
|
84%
|
146
|
5
|
e
|
2,4 Cl
|
H
|
64%
|
116-117
|
6
|
f
|
H
|
4-OMe
|
87%
|
141-143
|
7
|
g
|
4-Me
|
4-OMe
|
89%
|
149-151
|
8
|
h
|
4-OMe
|
4-Me
|
88%
|
133-134
|
9
|
i
|
4-Br
|
4-Me
|
86%
|
202-203
|
4
|
j
|
4Br
|
H
|
85%
|
150-152
|
4
|
k
|
H
|
4-NO2
|
76%
|
168
|
10
|
Choline chloride recyclability
![](data:image/png;base64,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)
Reusability is an essential feature of this process. Choline chloride is tested for its reusability in the production of benzylamine and 1, 2,3-triazoles. Ethyl acetate/H2O extracts the insoluble crude product, including choline chloride. The primitive residue is collected and re-crystallized with EtOH or acetone as the solvent and ethyl acetate as an anti-solvent. A new study has shown that choline chloride may be reused five times, albeit with decreased product output (Figure 1).