A simple and highly efficient solvent- and catalyst-free synthesis of novel N-sulfamoyl imines

Figures & data

Table 1. Synthesis of N-benzylidene-4-methoxyaniline under various temperatures.

Compound	Assay^a	Temperature (°C)	Time (h)	Yield^b (%)
III	1	25	3	/
	2	40	3	/
	3	50	3	/
	4	60	3	35
	5	100	0.5	94

^a Reaction conditions: benzaldehyde (1.1 mmol), p-anisidine (1 mmol).

^b Isolated yield.

Figure 1. Solvent-free synthesis of N-benzylidene-4-methoxyaniline.

Figure 2. Synthesis of N-chloroethylsulfamides.

Figure 3. Synthesis of N- and N,N-bis-chloroethylsulfamoyl imine.

Table 2. Synthesis of N-(2-chloroethylsulfamoyl) imines under catalyst-free and solventless conditions.

Entry	Rʹ	Sulfamoyl imine	Time (min)	Yield (%)
1a			50	80
2a			65	89
3a			60	90
4a			65	95
5a			65	92
6a			65	85
7a			60	90

Table 3. Synthesis of N,N-bis-(2-chloroethylsulfamoyl) imines under catalyst-free and solventless conditions.

Entry	Rʹ	Sulfamoyl imine	Time (min)	Yield (%)
1b			55	80
2b			65	89
3b			60	90
4b			65	95
5b			65	92
6b			65	85
7b			60	90
8b			60	82

Table 4. Effect of various solvents: ethanol, methanol, and toluene under refluxed conditions, and solvent-free conditions at 100°C.

Entry	Solvent	Time (h)	Yield (%)
1a	Methanol	24	/
1a	Ethanol	8	30
1a	Toluene	6	25
1a	Solvent-free	0.8	95