Acrylonitrile → HCID 21188082, compound

HRID 1383590Notes

Reaction equation

[C:1]([C:3]1[C:7](I)=[CH:6][N:5]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:4]=1)#[N:2].[C:21](#[N:24])[CH:22]=[CH2:23].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:1]([C:3]1[C:7](/[CH:23]=[CH:22]/[C:21]#[N:24])=[CH:6][N:5]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:4]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (0.864 g), acrylonitrile (0.264 g), triethylamine (0.4 ml), palladium acetate (0.04 g) and dimethylformamide (10 ml) were stirred under an atmosphere of nitogen at 70° C. for 24 hours. The reaction mixture was evaporated and the residue partitioned between water and dichloromethane. The organic layer was separated, washed with water, brine, then dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (40 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a white solid m.p. 144-145° C.

Workup

customThe reaction mixture was evaporated
customthe residue partitioned between water and dichloromethane
customThe organic layer was separated
washwashed with water, brine
dry with materialdried (Na2SO4)
customevaporated
customThe residue was purified by column chromatography on silica gel (40 g)
washeluted with dichloromethane
customCombination and evaporation of suitable fractions

Sources & evidence

ORD record: ord-d5b2184df6814c018e8685680ada8788
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255333B1

Reaction notes

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