Water → HCID 21183796, compound

HRID 1384793Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10].Br[CH2:15][CH2:16][CH:17]=[CH2:18].O>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:18][CH2:17][CH:16]=[CH2:15])[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of sodium hydride (14.8 g, 60% dispersion in mineral oil) in dimethylformamide (DMF, 150 ml) at 0° C. under nitrogen was added a solution of 3,4-dichlorophenylacetonitrile (68.9 g, 1 mol. equivalent) in DMF (300 ml) and the mixture was stirred for 3 hours. A solution of 4-bromobut-1-ene (50 g, 1 mol. eq.) in DMF (100 ml) was then added, and the mixture was stirred at room temperature for one hour, then heated to 60° C. for 5 hours. The reaction mixture was cooled and water (1 liter) was added. The mixture was then extracted with ethyl acetate (2×500 ml). The combined organic extracts were then washed with water (2×1 liter), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was then purified by column chromatography using silica gel, eluting with a solvent gradient of ethyl acetate:hexane (1:19 to 1:6, by volume) to give the title compound (51.5 g).

Workup

stirringthe mixture was stirred at room temperature for one hour
temperatureThe reaction mixture was cooled
extractionThe mixture was then extracted with ethyl acetate (2×500 ml)
washThe combined organic extracts were then washed with water (2×1 liter)
dry with materialdried over MgSO4
customthe solvent was removed under reduced pressure
customThe residue was then purified by column chromatography
washeluting with a solvent gradient of ethyl acetate:hexane (1:19 to 1:6, by volume)

Sources & evidence

ORD record: ord-dba6ad927ee64ed49ed5a08a9e8f6f28
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262046B1

Reaction notes

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