2-Chloro-5-nitrobenzenesulfonyl chloride → 97094-83-2

HRID 1199841Notes

Reaction equation

HRID 1199841 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[S:11](Cl)(=O)=O>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[SH:11]

Participants

3

Reactant 1

HCID 206302-Chloro-5-nitrobenzenesulfonyl chloride

Product 1

HCID 471301397094-83-2Yield 116.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A solution of anhydrous stannous chloride (152.5 g) in conc. hydrochloric acid (150 ml) was cooled to 0° C., and 2-chloro-5-nitrobenzenesulfonyl chloride (34.3 g) was added thereto while stirring. The resultant mixture was heated at 100° C. for 15 minutes while stirring, followed by being allowed to stand. Conc. hydrochloric acid (230 ml) was added to the reaction mixture. The precipitated crystals were collected by filtration, neutralized with a 4% aqueous sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried and concentrated to give 25.0 g of 2-chloro-5-aminothiophenol.

Workup

  1. stirringwhile stirring
  2. filtrationThe precipitated crystals were collected by filtration
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9fb76a6e55d478aaf5a528c7bc4f2c2
Source dataset
uspto-grants-1990_02
Patent number
US04902832

Reaction notes

Loading…