Thiophenol → HCID 21520097, compound

HRID 1605511Notes

Reaction equation

HRID 1605511 reaction equation
[CH2:1]([S:5][C:6]1[CH:7]=[C:8]([CH:14]=[C:15]([S:18](=[O:21])(=[O:20])[NH2:19])[C:16]=1Cl)[C:9]([O:11]CC)=[O:10])[CH2:2][CH2:3][CH3:4].[C:22]1([SH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1([S-])C=CC=CC=1.[Na+]>C(O)C>[CH2:1]([S:5][C:6]1[CH:7]=[C:8]([CH:14]=[C:15]([S:18](=[O:20])(=[O:21])[NH2:19])[C:16]=1[S:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 4110039Sodium benzenethiolateHCID 21520114HCID 21520114, compound

Product 1

HCID 21520097HCID 21520097, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-butylthio-4-chloro-5-sulfamylbenzoate (0.85 g), thiophenol (0.6 ml), and dry ethanol (25 ml) containing 5 millimoles of sodium thiophenolate is refluxed for 6 hours. After evaporation in vacuo 1 N sodium hydroxide (20 ml) and ethanol (10 ml) are added, and the mixture is refluxed for 15 minutes. After cooling and extraction with diethyl ether, 3-butylthio-4-phenylthio-5-sulfamylbenzoic acid is precipitated from the aqueous layer by addition of 4 N hydrochloric acid. The precipitate is collected by filtration and recrystallized from aqueous ethanol to yield the desired acid having a melting point of 192° - 193° C.

Workup

  1. temperatureis refluxed for 6 hours
  2. customAfter evaporation in vacuo 1 N sodium hydroxide (20 ml) and ethanol (10 ml)
  3. additionare added
  4. temperaturethe mixture is refluxed for 15 minutes
  5. temperatureAfter cooling
  6. extractionextraction with diethyl ether, 3-butylthio-4-phenylthio-5-sulfamylbenzoic acid
  7. customis precipitated from the aqueous layer by addition of 4 N hydrochloric acid
  8. filtrationThe precipitate is collected by filtration
  9. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-3b34266dddde4dae94d3429b4190b240
Source dataset
uspto-grants-1976_04
Patent number
US03950376

Reaction notes

Loading…