Ammonia → 5-(Chloromethyl)isoxazole-3-carboxamide

HRID 1952848Notes

Reaction equation

HRID 1952848 reaction equation
[NH3:1].[Cl:2][CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9](Cl)=[O:10])[CH:5]=1>C(Cl)Cl>[Cl:2][CH2:3][C:4]1[O:8][N:7]=[C:6]([C:9]([NH2:1])=[O:10])[CH:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 130018995-(Chloromethyl)-1,2-oxazole-3-carbonyl chloride

Product 1

HCID 218665415-(Chloromethyl)isoxazole-3-carboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ammonia was passed into a solution of 10 g (55.56 mmol) of 5-chloromethylisoxazole-3-carbonyl chloride in 100 ml of methylene chloride at 10-15° C. for 1 h, and the mixture was then stirred at room temperature for 1 h. After the solution had been cooled to 0° C., the precipitate was filtered off with suction and washed with a little cold methylene chloride, and the residue was extracted by stirring with water twice to remove ammonium salts. Drying under reduced pressure resulted in 6.58 g of pure product as a pale powder (74% of theory).

Workup

  1. temperatureAfter the solution had been cooled to 0° C.
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with a little cold methylene chloride
  4. extractionthe residue was extracted
  5. stirringby stirring with water twice
  6. customto remove ammonium salts
  7. customDrying under reduced pressure

Sources & evidence

ORD record
ord-24ed384826b94109bc700eb6b8178389
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

Loading…