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

HRID 1582905Notes

Reaction equation

HRID 1582905 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

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. filtrationthe precipitate was filtered off with suction
  2. washwashed with a little cold methylene chloride
  3. extractionthe residue was extracted twice
  4. stirringby stirring with water
  5. customto remove the ammonium salts
  6. customDrying in vacuo

Sources & evidence

ORD record
ord-ef335c7c91cc47a196ed1e8cd5354d4f
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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