Thionyl Chloride → HCID 23447867, compound

HRID 840119Notes

Reaction equation

HRID 840119 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=O)=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([Cl:18])=[O:15])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 234478853-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acid

Product 1

HCID 23447867HCID 23447867, compound

Procedure

A solution of 0.3 g of Compound 8D in 1.05 mL of thionyl chloride was refluxed for 1 h under N2 atmosphere. After cooling to r.t., the solvent was evaporated to dryness and the so obtained crude 3-(4-fluorophenyl)isoxazole-4-carbonyl chloride dissolved in 10 mL of chloroform. Afterwards a solution of 0.48 g of Compound 8B and 0.6 mL of triethylamine in 10 mL of chloroform was added and the resulting mixture stirred at r.t. for 18 h. The solvent was washed with water, dried (sodium sulphate), filtered and evaporated in vacuo. The crude was purified by flash chromatography (ethyl acetate-2N ammonia in methanol 95:5) to give 0.607 g (79.8%) of the title compound. M.p.: 122.4-123° C.

Workup

  1. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-5ea0a5956caa42928b40ac22774730e2
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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