Hydrochloric Acid → HCID 54022017, compound

HRID 1282794Notes

Reaction equation

HRID 1282794 reaction equation
[CH2:1]([S:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].Cl.[CH3:27]O>>[CH2:1]([S:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:24])(=[O:25])[NH2:23])[C:14]=1[O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:9]([O:11][CH3:27])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 54574929HCID 54574929, compound

Product 1

HCID 54022017HCID 54022017, compound

Procedure

A mixture of 3-n-butylthio-4-phenoxy-5-sulfamylbenzoic acid (2.5 g) and methanol (75 ml) is saturated with gaseous hydrogen chloride. The reaction mixture is allowed to warm during saturation. After cooling and standing for 5 hours, the reaction mixture is evaporated in vacuo. The residue is triturated with water and sufficient sodium hydrogen carbonate to neutralize traces of hydrochloric acid. The precipitated methyl 3-n-butylthio-4-phenoxy-5-sulfamylbenzoate is collected and recrystallized from methanol/water to yield the ester with a melting point of 122°-123°C.

Workup

  1. temperatureto warm during saturation
  2. temperatureAfter cooling
  3. customthe reaction mixture is evaporated in vacuo
  4. customThe residue is triturated with water and sufficient sodium hydrogen carbonate
  5. customThe precipitated methyl 3-n-butylthio-4-phenoxy-5-sulfamylbenzoate is collected
  6. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-29f4fe4e8f0d421e9091696021ec9222
Source dataset
uspto-grants-1976_08
Patent number
US03972886

Reaction notes

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