Benzenesulfonyl chloride, 4-chloro-3-nitro- → 3-amino-4-chlorobenzenethiol

HRID 1512972Notes

Reaction equation

HRID 1512972 reaction equation
[Sn].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=O)=O)=[CH:5][C:4]=1[N+:13]([O-])=O>Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][C:4]=1[NH2:13]

Participants

4

Reactant 2

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 5352426Tin atom

Product 1

HCID 6406993-amino-4-chlorobenzenethiolYield 73.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a mixture of concentrated hydrochloric acid (30 mL) and ice (25 g) was added tin (29.7 g) under ice-cooling, followed by adding 4-chloro-3-nitrobenzenesulfonyl chloride (6.4 g), and the mixture was stirred under ice-cooling for 1.5 hours, and then stirred at 90° C. for 2 hours. The insoluble material was removed by filtration, and the filtrate was stirred at room temperature overnight. The precipitated crystals were collected by filtration. The collected crystals were washed with water, and dried under reduced pressure to give the title compound (2.95 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1.5 hours
  3. stirringstirred at 90° C. for 2 hours
  4. customThe insoluble material was removed by filtration
  5. stirringthe filtrate was stirred at room temperature overnight
  6. filtrationThe precipitated crystals were collected by filtration
  7. washThe collected crystals were washed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-53fa4a2a38bf49118caa5aeffe7e6413
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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