Thionyl Chloride → HCID 23447867, compound

HRID 1840292Notes

Reaction equation

HRID 1840292 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-a3b72c1f57f24594b9886db34f4bb87a
Source dataset
uspto-grants-2004_01
Patent number
US06680319B2

Reaction notes

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