Water → 3-Ethyl-4-chloro-5-acetylaminoisoxazole

HRID 482908Notes

Reaction equation

HRID 482908 reaction equation
[CH2:1]([C:3]1[CH:7]=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[O:5][N:4]=1)[CH3:2].ClCl.[Cl:14]C(Cl)(Cl)Cl.O>C(O)(=O)C>[CH2:1]([C:3]1[C:7]([Cl:14])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[O:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 133364373-Ethyl-5-acetylaminoisoxazoleHCID 86737392Chlorine tetrachloromethane

Product 1

HCID 133364383-Ethyl-4-chloro-5-acetylaminoisoxazoleYield 203.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Ethyl-5-acetylaminoisoxazole (1) (1.98 g) was dissolved in acetic acid (15 ml), chlorine-tetrachloromethane (18 ml, containing 1.09 g of chlorine) was added thereto under stirring at room temperature and after addition of water the mixture was extracted with chloroform after 5 minutes. The extract was washed with water, dried over sodium sulfate and evaporated. The resulting crystalline residue was recrystallized from ether/hexane to give 3-ethyl-4-chloro-5-acetylaminoisoxazole (2) (1.86 g), mp. 113°-114° C.

Workup

  1. extractionwas extracted with chloroform after 5 minutes
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe resulting crystalline residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-45ec15bca8cb4f64a57ae8e988b77363
Source dataset
uspto-grants-1986_03
Patent number
US04576956

Reaction notes

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