Methanol → HCID 21440142, compound

HRID 328971Notes

Reaction equation

HRID 328971 reaction equation
[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[S:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26]O>S(=O)(=O)(O)O>[CH2:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([O:14][CH3:26])=[O:13])=[CH:10][C:9]=1[S:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 54516912HCID 54516912, compound

Product 1

HCID 21440142HCID 21440142, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-benzyl-3-n-butylthio-5-sulfamylbenzoic acid (0.85 g) in dry methanol (10 ml) and conc. sulfuric acid (0.2 ml) is refluxed for 20 hours. The methanol is removed in vacuo and the residue is triturated with 1 N sodium hydrogen carbonate (15 ml). The resulting crystalline material is collected by filtration, washed with water and dried. After recrystallization from methanol, methyl 4-benzyl-3-n-butylthio-5-sulfamylbenzoate is obtained with a melting point of 118°-120° C.

Workup

  1. customThe methanol is removed in vacuo
  2. customthe residue is triturated with 1 N sodium hydrogen carbonate (15 ml)
  3. filtrationThe resulting crystalline material is collected by filtration
  4. washwashed with water
  5. customdried
  6. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-7cb3606ffa7a47c989205b00357508f7
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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