4-Chlorobenzonitrile → HCID 57750306, compound

HRID 423105

Reaction equation

[Li+].CCC[CH2-].[CH3:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1>C1COCC1>[Cl:12][C:13]1[CH:20]=[CH:19][C:16](/[C:17](/[NH2:18])=[CH:6]/[C:7]2[S:8][CH:9]=[CH:10][N:11]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A 2.5M solution of N-butyllithium (8.00 mL, 20.00 mmol) in hexanes, was added dropwise to 2-methylthiazole (1.983 g, 20 mmol) dissolved in THF (35.00 mL) over a period of 5 minutes under argon at −70° C. The resulting pale yellow slurry was stirred at −70° C. for 2.5 hour. 4-chlorobenzonitrile (2.75 g, 20.00 mmol) in THF (35.00 mL) was added dropwise to the suspension, which was stirred at −70° C. for 90 minutes after the end of the addition. The reaction mixture was allowed to warm to room temperature under stirring and darkened. The crude was concentrated to dryness and diluted with ethyl acetate then washed with water, dried over magnesium sulphate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 10 to 100% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford (Z)-1-(4-chlorophenyl)-2-(thiazol-2-yl)ethenamine (1.466 g, 31.0%) as a pale yellow solid.

Workup

stirringwas stirred at −70° C. for 90 minutes
additionafter the end of the addition
temperatureto warm to room temperature
stirringunder stirring
concentrationThe crude was concentrated to dryness
additiondiluted with ethyl acetate
washthen washed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated
customThe crude product was purified by flash chromatography on silica gel eluting with 10 to 100% ethyl acetate in dichloromethane
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-39b6bfe9ef8a414ea5978e6c0eb883e2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101623B2

Linked notes

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