Peracetic Acid → Sufotidine

HRID 652099Notes

Reaction equation

HRID 652099 reaction equation
[C:1](OO)(=O)C.[CH3:6][N:7]1[C:11]([NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:18]=2)=[N:10][C:9]([CH2:30]SC)=[N:8]1.C([O-])(=O)C.[Na+].[S:38]([O-:41])([O-])=[O:39].[Na+].[Na+]>C(O)(=O)C>[CH3:6][N:7]1[C:11]([NH:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:18]=2)=[N:10][C:9]([CH2:30][S:38]([CH3:1])(=[O:41])=[O:39])=[N:8]1

Participants

6

Reactant 4

HCID 6585Peracetic AcidHCID 24437Sodium SulfiteHCID 517045Sodium AcetateHCID 12774362HCID 12774362, compound

Product 1

HCID 71763Sufotidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Peracetic acid (1.05 ml of a 6.1M solution) in acetic acid (7 ml) was added to an ice-cooled solution of 1-methyl-3-methylthiomethyl-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine (0.82 g) in acetic acid (10 ml) with sodium acetate (0.52 g). The mixture was stirred at room temperature for 18 h, sodium sulphite (1.25 g) added and the mixture evaporated to dryness. The residue was basified to pH 8 with sodium bicarbonate solution, washed with ethyl acetate, basified to pH 10 with sodium carbonate and extracted with ethyl acetate to give a foam (0.46 g). This was crystallised from methyl acetate-petroleum ether (b.p. 60°-80°) to give the title compound as a white solid (0.22 g), m.p. 121°-122°.

Workup

  1. customthe mixture evaporated to dryness
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-57631e0af2e6456ca896df9b00a129e3
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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