Acetic Acid → Ethyl 2-acetylamino-4-thiazoleacetate

HRID 1369203Notes

Reaction equation

HRID 1369203 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[C:13](O)(=[O:15])[CH3:14]>C(OC(=O)C)(=O)C>[C:13]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 3477732Ethyl 2-acetylamino-4-thiazoleacetateYield 91%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Ethyl 2-amino-4-thiazoleacetate (3.72 g 20 mmole) was taken up in acetic acid (4 mL) and acetic anhydride (4 mL), and the resulting suspension was heated at reflux for 3 hr. Concentration and flash chromatography on silica gel (5% MeOH/CH2H2) gave the title compound (4.1 g, 91%) as a white solid: MS (ES) m/e 229 (M+H)+.

Workup

  1. temperatureat reflux for 3 hr
  2. concentrationConcentration and flash chromatography on silica gel (5% MeOH/CH2H2)

Sources & evidence

ORD record
ord-b4e0353fe30d437eb6983e3cd6c4c51b
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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