Acetic Anhydride → 2(3H)-Thiazolethione, 3-(acetyloxy)-4-methyl-

HRID 2082015Notes

Reaction equation

HRID 2082015 reaction equation
[OH:1][N:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]1=[S:8].C(=O)(O)[O-].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15]>O>[C:14]([O:1][N:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]1=[S:8])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 3415933-Hydroxy-4-methyl-2(3H)-thiazolethioneHCID 516892Sodium Bicarbonate

Product 1

HCID 101303022(3H)-Thiazolethione, 3-(acetyloxy)-4-methyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.74 parts of 3-hydroxy-4-methylthiazol-2-(3H)-thione, 0.84 parts of sodium bicarbonate and 30 parts of water were stirred at 0°-5° C. while 0.52 parts of acetic anhydride were added dropwise and the reaction mixture was stirred at 0°-5° C. for a further hour. A precipitate was formed which was separated by filtration and recrystallised from aqueous methanol. 0.33 parts of 3-acetoxy-4-methylthiazol-2(3H)-thione, of melting points 100°-101° C., was obtained.

Workup

  1. additionwere added dropwise
  2. customA precipitate was formed which
  3. customwas separated by filtration
  4. customrecrystallised from aqueous methanol

Sources & evidence

ORD record
ord-bcc9f4840dad4b9b8c6f5aa54c2818cd
Source dataset
uspto-grants-1993_02
Patent number
US05187172

Reaction notes

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