Ammonia → 5-(Chloromethyl)isoxazole-3-carboxamide
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- filtrationthe precipitate was filtered off with suction
- washwashed with a little cold methylene chloride
- extractionthe residue was extracted twice
- stirringby stirring with water
- customto remove the ammonium salts
- customDrying in vacuo
Sources & evidence
- ORD record
- ord-ef335c7c91cc47a196ed1e8cd5354d4f
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06740647B1
Reaction notes
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