Benzenemethanamine, 3,4-dichloro- → N-(3,4-dichlorobenzyl)-2-nitrobenzenesulfonamide

HRID 1639290Notes

Reaction equation

HRID 1639290 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6].C(N(CC)CC)C.[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28])([O-:20])=[O:19]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:6][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N+:18]([O-:20])=[O:19])(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 1000717N-(3,4-dichlorobenzyl)-2-nitrobenzenesulfonamideYield 84.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 3,4-dichlorobenzylamine (3.97 g) and triethylamine (3.5 ml) in chloroform (80 ml) was added a solution of 2-nitrobenzenesulfonyl chloride (5 g) in chloroform (20 ml) at 0° C. with stirring and the mixture was stirred for 30 minutes at the same temperature. The reaction mixture was washed successively with diluted hydrochloric acid and water, and then dried. Evaporation of the solvent gave N-(3,4-dichlorobenzyl)-2-nitrobenzenesulfonamide (6.87 g).

Workup

  1. stirringthe mixture was stirred for 30 minutes at the same temperature
  2. washThe reaction mixture was washed successively with diluted hydrochloric acid and water
  3. customdried
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-115cb02a4fb74f12b670f1b59d3c6b25
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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