Benzoyl chloride → 3-(Benzoyloxy)-4-methyl-1,3-thiazole-2(3H)-thione

HRID 2082014Notes

Reaction equation

HRID 2082014 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](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[C:14]([O:1][N:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]1=[S:8])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 3415933-Hydroxy-4-methyl-2(3H)-thiazolethioneHCID 516892Sodium Bicarbonate

Product 1

HCID 233556233-(Benzoyloxy)-4-methyl-1,3-thiazole-2(3H)-thione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.735 parts of 3-hydroxy-4-methylthiazol-2(3H)-thione were stirred in 50 parts of water and 0.84 parts of sodium hydrogen carbonate. The solution was screened and 0.9 parts of benzoyl chloride were added. The reaction mixture was stirred overnight at room temperature. A precipitate was formed which was separated by filtration, washed with cold water and recrystallised from ethanol to give 3-benzoyloxy-4-methylthiazol-2(3H)-thione, m.pt. 100°-102° C. By analysis the composition was found to be C, 52.4% wt; H, 3.6% wt; N, 5.6% wt and S, 25% wt. C11H9NO2S2 requires C, 52.6% wt; H, 3.6% wt; N, 5.6% wt and S, 25.5% wt.

Workup

  1. customA precipitate was formed which
  2. customwas separated by filtration
  3. washwashed with cold water
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-356595daa9bb4a95a04b333873f6d66f
Source dataset
uspto-grants-1993_02
Patent number
US05187172

Reaction notes

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