Water → (2-Acetamido-1,3-thiazol-4-yl)methyl acetate

HRID 2117829Notes

Reaction equation

HRID 2117829 reaction equation
Cl.[C:2]([O:5][CH2:6][C:7]1[N:8]=[C:9]([NH2:12])[S:10][CH:11]=1)(=[O:4])[CH3:3].N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20].O>ClCCl>[C:2]([O:5][CH2:6][C:7]1[N:8]=[C:9]([NH:12][C:19](=[O:21])[CH3:20])[S:10][CH:11]=1)(=[O:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 21915032(2-Aminothiazol-4-yl)methyl acetate hydrochloride

Product 1

HCID 14931747(2-Acetamido-1,3-thiazol-4-yl)methyl acetateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2-amino-1,3-thiazol-4-yl)methyl acetate hydrochloride (56 g) and pyridine (45 g) in dichloromethane (560 ml) was added acetyl chloride (23 g) over a period of 30 minutes at 5° C., and the reaction mixture was stirred for 10 minutes at the same temperature. The reaction mixture was poured into water (500 ml) and extracted with chloroform (1 L). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residual solid was collected by filtration with isopropyl ether to give (2-(acetylamino)-1,3-thiazol-4-yl)methyl acetate (47 g) as white crystals.

Workup

  1. extractionextracted with chloroform (1 L)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. filtrationThe residual solid was collected by filtration with isopropyl ether

Sources & evidence

ORD record
ord-c498a4f57a314cc89a82283683fdf41e
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

Loading…