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

HRID 569802
Notes
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Reaction equation

HRID 569802 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-0c4e7d0d82644df5aa8e00817b1b38f7
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04734419

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes