Potassium Carbonate → 2-Acetylamino-5-(4-methoxyphenylthio)thiazole

HRID 1656981Notes

Reaction equation

HRID 1656981 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 46841342-Acetamido-5-chlorothiazole

Product 1

HCID 157291822-Acetylamino-5-(4-methoxyphenylthio)thiazoleYield 78.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-acetylamino-5-chlorothiazole (1.76 g), 4-methoxythiophenol (1.5 g) and potassium carbonate (2.0 g) in N,N-dimethylformamide (30 ml) was heated at 120° C. for 3.5 hours with stirring. The reaction mixture was poured into ice water and the precipitates were collected by filtration to give solid. The solid was recrystallized from ethanol to give 2-acetylamino-5-(4-methoxyphenylthio)thiazole (2.2 g, Yield: 78.6%). mp: 190°-191° C. IR (Nujol): 3175, 1695, 1565, 1490, 1295, 1250 cm-1

Workup

  1. filtrationthe precipitates were collected by filtration
  2. customto give solid
  3. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-4bdc4a34e24b41eab902aafab49454a2
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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