Triethylamine → 3-(2,6-dimethylphenylamino)-2-butanone O-methyloxime

HRID 46580Notes

Reaction equation

C(N(CC)CC)C.Cl.[CH3:9][O:10][NH2:11].[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[NH:20][CH:21]([CH3:25])[C:22](=O)[CH3:23]>ClCCl>[CH3:9][O:10][N:11]=[C:22]([CH:21]([NH:20][C:14]1[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:13]=1[CH3:12])[CH3:25])[CH3:23]

Participants

Conditions

Temperature: 20 °C

Procedure

A sample of 50.5 g triethylamine was added dropwise to a solution of 50.1 g (0.6 mol) methoxyamine hydrochloride in 75 ml dichloromethane at 9°-20° C. To the resulting solution was added about one-half of a 95.6-g (0.5-mol) sample of 3-(2,6-dimethylphenylamino)-2-butanone. The reaction temperature rose from 16° C. to 30° C. The reaction mixture was cooled in an ice bath, and the remaining 3-(2,6-dimethylphenylamino)-2-butanone was added dropwise. The reaction mixture was then stirred about 18 hours at about 20° C., washed with 50 ml of water and evaporated under reduced pressure to give 100.3 g of 3-(2,6-dimethylphenylamino)-2-butanone O-methyloxime, as an oil. The nuclear magnetic resonance spectrum showed a sharp 3-proton singlet (--OCH3) at 3.9 ppm (relative to tetramethylsilane) and a sharp 6-proton singlet (2,6-dimethyl groups) at 2.2 ppm.

Workup

customrose from 16° C. to 30° C
temperatureThe reaction mixture was cooled in an ice bath
washwashed with 50 ml of water
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-8c9f8b193ed54ce892b4c0d2477e7e72
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04174210

Reaction notes

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