3,5-Dimethylisoxazole-4-sulfonyl chloride → HCID 19068786, compound

HRID 1957254Notes

Reaction equation

HRID 1957254 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:20][C:21]1[C:25]([S:26](Cl)(=[O:28])=[O:27])=[C:24]([CH3:30])[O:23][N:22]=1>C1(C)C=CC=CC=1.N1C=CC=CC=1>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)=[CH:3][C:2]=1[NH:1][S:26]([C:25]1[C:21]([CH3:20])=[N:22][O:23][C:24]=1[CH3:30])(=[O:28])=[O:27]

Participants

5

Reactant 2

HCID 27363193,5-Dimethylisoxazole-4-sulfonyl chlorideHCID 15766880HCID 15766880, compound

Product 1

HCID 19068786HCID 19068786, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A solution of 2.5 g of 2-(3-amino-4-chlorophenyl)-3-chloro-5-trifluoromethylpyridine and 2.3 g of 3,5-dimethylisoxazole-4-sulfonyl chloride in a mixture of 100 ml of toluene and 100 ml of pyridine was refluxed for 16 hours. The mixture was concentrated and the residue was taken up in 50 ml of ethyl acetate. The solution was washed with 50 ml each of 10% strength hydrochloric acid and 10% strength aqueous sodium bicarbonate solution and was dried over sodium sulfate and concentrated. Chromatography on silica gel with cyclohexane/ethyl acetate (6:1) resulted in 1.9 g of colorless crystals; melting point: 161°-162° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationThe mixture was concentrated
  3. washThe solution was washed with 50 ml each of 10% strength hydrochloric acid and 10% strength aqueous sodium bicarbonate solution
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-777a7276b9fe472fb762b8a01c884b7f
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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