Dimethylformamide → 2-Propionylamino-4-chloromethylthiazole

HRID 1252050Notes

Reaction equation

HRID 1252050 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][Cl:9])[N:7]=1.CN(C)C=O.[C:15](Cl)(=[O:18])[CH2:16][CH3:17]>N1C=CC=CC=1>[C:15]([NH:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][Cl:9])[N:7]=1)(=[O:18])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 62324Propionyl chlorideHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 103980162-Propionylamino-4-chloromethylthiazoleYield 50.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-amino-4-chloromethylthiazole hydrochloride (50 g), anhydrous N,N-dimethylformamide (250 ml) and anhydrous pyridine (50 ml) was added dropwise propionyl chloride (30 g) keeping the temperature below 3° C. with stirring and the mixture was stirred for 20 minutes at the same temperature. The reaction mixture was poured into ice water (1500 ml) and stirred. The crystal was collected by filtration and washed with water to give 2-propionylamino-4-chloromethylthiazole (28.15 g).

Workup

  1. customthe temperature below 3° C.
  2. stirringthe mixture was stirred for 20 minutes at the same temperature
  3. stirringstirred
  4. filtrationThe crystal was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-8e8a672ea0f1401db3ffc3191c2a785e
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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