Pyridine → 2-chloro-N-(5-methylisoxazol-3-yl)acetamide

HRID 2397597Notes

Reaction equation

HRID 2397597 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.N1C=CC=CC=1.[Cl:14][CH2:15][C:16](Cl)=[O:17]>C(Cl)(Cl)Cl>[Cl:14][CH2:15][C:16]([NH:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1)=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 661723-Amino-5-methylisoxazole

Product 1

HCID 5666612-chloro-N-(5-methylisoxazol-3-yl)acetamideYield 59.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 800 ml of chloroform is added 118 grams (1.12 moles) of 3-amino-5-methylisoxazole followed by 118 grams (1.5 moles) of pyridine. To this solution is added 147 grams (1.3 moles) of chloroacetylchloride with the addition temperature maintained at 0°-10° C. The reaction is then stirred at room temperature for 1 hour, filtered and dried in a vacuum desiccator to give 116 grams (56%) of 3-(chloroacetamido)-5-methylisoxazole, mp 192°-195° C. This material is slightly irritating to the skin and due caution should be exercised.

Workup

  1. temperaturemaintained at 0°-10° C
  2. filtrationfiltered
  3. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-4861525cf2d345b9b4ed60c6422d9329
Source dataset
uspto-grants-1977_05
Patent number
US04022796

Reaction notes

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