Water → HCID 21914785, compound

HRID 2117891Notes

Reaction equation

HRID 2117891 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[C:19](Cl)(=[O:21])[CH3:20].O>N1C=CC=CC=1>[C:19]([NH:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 21914710HCID 21914710, compound

Product 1

HCID 21914785HCID 21914785, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-amino-5-[4-(methylthio)phenyl]-1,3-thiazole-4-carboxylate (8.8 g) was dissolved in pyridine (88 ml), and then acetyl chloride (6.7 ml) was added dropwise to the solution at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 30 minutes and at 50° C. for 2 hours. After cooled to 0° C., water was added to the solution. The precipitate was filtered in vacuo, and the solid was washed with ethyl ether to give methyl 2-(acetylamino)-5-[4-(methylthio)phenyl]-1,3-thiazole-4-carboxylate (9.3 g) as an off-white solid.

Workup

  1. temperatureAfter cooled to 0° C.
  2. filtrationThe precipitate was filtered in vacuo
  3. washthe solid was washed with ethyl ether

Sources & evidence

ORD record
ord-6f36cda0366640efa51a8d1254cd1f85
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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