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

HRID 569803Notes

Reaction equation

HRID 569803 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

4

Reactant 1

HCID 1000717N-(3,4-dichlorobenzyl)-2-nitrobenzenesulfonamide

Product 1

HCID 37280272-amino-N-(3,4-dichlorobenzyl)benzenesulfonamideYield 92.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

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

  1. temperatureAfter cooling
  2. filtrationthe iron was filtered off
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. customRecrystallization from ethyl ether

Sources & evidence

ORD record
ord-bb18963c1b3f4082bd9183a4a7b60aaa
Source dataset
uspto-grants-1988_03
Patent number
US04734419

Reaction notes

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