Ammonia → HCID 21520060, compound

HRID 1605520Notes

Reaction equation

HRID 1605520 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:25](Cl)(=[O:27])=[O:26])[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:29]>>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:25](=[O:27])(=[O:26])[NH2:29])[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 21520076HCID 21520076, compound

Product 1

HCID 21520060HCID 21520060, compound

Procedure

3-Benzylthio-5-chlorosulfonyl-4-phenoxybenzoic acid (0.6 g) is added to concentrated aqueous ammonia (10 ml). After 1 hour, the reaction mixture is heated on a steam-bath for 15 minutes, and crude 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid precipitated by addition of a 1 N hydrochloric acid until pH 2.5. The crude product is dissolved in aqueous sodium hydrogen carbonate by heating. After cooling, the precipitated sodium salt of 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration. The salt is redissolved in hot water (20 ml) and 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid precipitated by addition of 1 N hydrochloric acid. After cooling and collecting by filtration, and drying in vacuo at 80° C, the compound is obtained with a melting point of 235°-236° C.

Workup

  1. temperaturethe reaction mixture is heated on a steam-bath for 15 minutes
  2. customcrude 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid precipitated by addition of a 1 N hydrochloric acid until pH 2.5
  3. dissolutionThe crude product is dissolved in aqueous sodium hydrogen carbonate
  4. temperatureby heating
  5. temperatureAfter cooling
  6. filtrationthe precipitated sodium salt of 3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid is collected by filtration
  7. dissolutionThe salt is redissolved in hot water (20 ml)
  8. custom3-benzylthio-4-phenoxy-5-sulfamylbenzoic acid precipitated by addition of 1 N hydrochloric acid
  9. temperatureAfter cooling
  10. filtrationcollecting by filtration
  11. customdrying in vacuo at 80° C
  12. customthe compound is obtained with a melting point of 235°-236° C.

Sources & evidence

ORD record
ord-3104724dadcd4007bbcb21113935a775
Source dataset
uspto-grants-1976_04
Patent number
US03950376

Reaction notes

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