N-(3,4-dichlorobenzyl)-2-nitrobenzenesulfonamide → 2-amino-N-(3,4-dichlorobenzyl)benzenesulfonamide

HRID 1639291Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)(=[O:9])=[O:8]>C(O)(=O)C.[Fe]>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:7]([NH:6][CH2:5][C:4]1[CH:19]=[CH:20][C:21]([Cl:22])=[C:2]([Cl:1])[CH:3]=1)(=[O:9])=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(3,4-dichlorobenzyl)-2-nitrobenzenesulfonamide (4 g) and iron (2 g) in acetic acid (30 ml) was stirred at 100° C. for 45 minutes. After cooling, the iron was filtered off. The filtrate was made alkaline with a diluted aqueous sodium hydroxide and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. Recrystallization from ethyl ether gave 2-amino-N-(3,4-dichlorobenzyl)benzenesulfonamide (3.40 g).

Workup

temperatureAfter cooling
filtrationthe iron was filtered off
extractionextracted with ethyl acetate
washThe extract was washed with water
customdried
customevaporated
customRecrystallization from ethyl ether

Sources & evidence

ORD record: ord-8c87543665ec4a8aac35ca58d689ae56
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04883800

Reaction notes

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