4-Chloro-N-(1,1-dimethyl-2-propynyl)benzamide → 2-(4-Chlorophenyl)-4,5-dihydro-4,4-dimethyl-5-methyleneoxazole

HRID 1107059Notes

Reaction equation

[CH3:1][C:2]([NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:5])[C:3]#[CH:4]>[Cu]Cl.C(OCCCC)(=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[O:15][C:3](=[CH2:4])[C:2]([CH3:1])([CH3:5])[N:6]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A round bottom flask was charged with N-(3-methylbutyn-3-yl)-4-chlorobenzamide (4.5 g, 19.09 mmol), copper(I) chloride (9.5 mg, 0.5 mol %), and n-butyl acetate (20 mL). The resulting mixture was heated to 95° C. for 4 h, then cooled to room temperature. The reaction was washed with 1 M hydrochloric acid solution and with water. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, and the residue was dried in a vacuum oven to afford 2-(4-chlorophenyl)-4,4-dimethyl-5-methyleneoxazoline (4.24 g, 94% yield) as a pale yellow oil (bp 95° C., 0.6 mm Hg).

Workup

temperaturecooled to room temperature
washThe reaction was washed with 1 M hydrochloric acid solution and with water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customThe solvent was removed by evaporation under reduced pressure
customthe residue was dried in a vacuum oven

Sources & evidence

ORD record: ord-c58de19889f94a969e34a18c6c4e3933
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057477

Reaction notes

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