Chloroacetyl chloride → 2-chloro-N-(1,2-oxazol-3-yl)acetamide

HRID 404623Notes

Reaction equation

HRID 404623 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[O:6]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7]1>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:11][C:8]1[CH:9]=[CH:10][O:6][N:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 18102163-Isoxazolamine

Product 1

HCID 133629182-chloro-N-(1,2-oxazol-3-yl)acetamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloroacetyl chloride (0.21 ml, 2.66 mmol) was dissolved in DCM (10 ml) and the solution was cooled to 0° C. with an ice-bath. Isoxazol-3-amine (0.41 ml, 5.58 mmol) was added dropwise and a white suspension was obtained. The mixture was stirred at room temperature for 2 hours, then the suspension was evaporated and the residue was purified by flash chromatography (ether/EtOAc=8/2 to 7/3) to obtain 2-chloro-N-(isoxazol-3-yl)acetamide (367 mg, 86% yield) as an off-white solid.

Workup

  1. customa white suspension was obtained
  2. customthe suspension was evaporated
  3. customthe residue was purified by flash chromatography (ether/EtOAc=8/2 to 7/3)

Sources & evidence

ORD record
ord-aa31ae0b32454c0daddf5894e3e54c2b
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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