Chlorine → HCID 13336443, compound

HRID 482909Notes

Reaction equation

HRID 482909 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:16]Cl>O1CCCC1.C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2[C:11]([Cl:16])=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 827181Acetamide, N-(3-phenyl-5-isoxazolyl)-

Product 1

HCID 13336443HCID 13336443, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Phenyl-5-acetylaminoisoxazole (7) (2.022 g) was dissolved in tetrahydrofuran (50 ml), a solution of chlorine (850 mg) in carbon tetrachloride (8.8 ml) was added dropwise thereto, and the mixture was kept to react at room temperature and under ice-cooling for 30 minutes, respectively. After evaporation the resulting residue was subjected to column chromatography on silica gel (20 g) to give crystals (1.43 g) of 3-phenyl-4-chloro-5-acetylaminoisoxazole (8) from the ether fractions; mp. 141°-141.5° C. (recrystallized from ether-hexane).

Workup

  1. customto react at room temperature and under ice-
  2. temperaturecooling for 30 minutes
  3. customAfter evaporation the resulting residue

Sources & evidence

ORD record
ord-5229bfbfbee144f98854b17eaa8902c8
Source dataset
uspto-grants-1986_03
Patent number
US04576956

Reaction notes

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