Ammonium Chloride → HCID 59443057, compound

HRID 1959118Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=O)=[C:4]([OH:17])[CH:3]=1.[C:18]([CH2:23][CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=[O:19].[Cl-].[NH4+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:23]([CH3:24])[C:18](=[O:19])[O:17]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of (4-chloro-2-hydroxyphenyl)(4-fluorophenyl)methanone (200 mg) and (carboethoxyethylidene)triphenylphosphorane (435 mg) was heated with stirring at 200° C. for 15 hours. After cooling, the reaction mixture was diluted with ethyl acetate and the solution was poured into an aqueous saturated ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine, and filtered through a column of porous diatomite (Chem Elut). The filtrate was concentrated and the resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=97/3 to 90/10) to give the titled compound (119 mg) as a yellow powder.

Workup

temperaturewas heated
temperatureAfter cooling
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with water and brine
filtrationfiltered through a column of porous diatomite (Chem Elut)
concentrationThe filtrate was concentrated
customthe resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=97/3 to 90/10)

Sources & evidence

ORD record: ord-cb957e44eb8a4e808eba783a7802c87d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410166B2

Reaction notes

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