Thiophenol → HCID 21506048, compound

HRID 1287749Notes

Reaction equation

HRID 1287749 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(=O)(O)[O-].[Na+]>[N+:15]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[S:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([OH:8])=[O:7])([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 21506048HCID 21506048, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (28 g), thiophenol (10.25 ml), and 1N sodium bicarbonate (300 ml) was refluxed for 3 hours. After cooling, the precipitated sodium salt of 3-nitro-4-phenylthio-5-sulphamyl-benzoic acid was filtered off. The sodium salt was dissolved in hot water (200 ml), and 3-nitro-4-phenylthio-5-sulphamyl-benzoic acid was precipitated by the addition of 4N hydrochloric acid until the pH was 1. After isolation and recrystallization from aqueous ethanol, the acid was obtained with a melting point of 245°-247° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated sodium salt of 3-nitro-4-phenylthio-5-sulphamyl-benzoic acid was filtered off
  4. dissolutionThe sodium salt was dissolved in hot water (200 ml)
  5. custom3-nitro-4-phenylthio-5-sulphamyl-benzoic acid was precipitated by the addition of 4N hydrochloric acid until the pH was 1
  6. customAfter isolation and recrystallization from aqueous ethanol
  7. customthe acid was obtained with a melting point of 245°-247° C.

Sources & evidence

ORD record
ord-0252bb0d546649128ba2f6cc4b73c63d
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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