Pyridine → Ethyl 2-acetamido-1,3-thiazole-4-carboxylate

HRID 2117848Notes

Reaction equation

HRID 2117848 reaction equation
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([NH:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 16495520Ethyl 2-aminothiazole-4-carboxylate hydrobromide

Product 1

HCID 702548Ethyl 2-acetamido-1,3-thiazole-4-carboxylateYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold mixture of ethyl 2-amino-1,3-thiazole-4-carboxylate hydrobromide (80 g), pyridine (52.5 g) and dichloromethane (800 ml) was added acetyl chloride (27.3 g) dropwise at 0° C., and the mixture was stirred for 30 minutes at the same temperature. The reaction mixture was washed with water (500 ml), dried over sodium sulfate and concentrated in vacuo. The crystalline residue was collected and washed with ethyl acetate to give ethyl 2-(acetylamino)-1,3-thiazole-4-carboxylate (60 g).

Workup

  1. washThe reaction mixture was washed with water (500 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crystalline residue was collected
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-40cbf9f3112b4c81a9aa7ddc9b4da7c6
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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