Hydroxylamine, O-ethyl- → HCID 178449937, compound

HRID 1380164Notes

Reaction equation

[C:1]([CH:6]1[C:11](=[O:12])[CH:10]([CH3:13])[CH:9]([CH2:14][CH:15]([S:17][CH2:18][CH3:19])[CH3:16])[CH2:8][C:7]1=[O:20])(=O)[CH2:2][CH2:3][CH3:4].[CH2:21]([O:23][NH2:24])[CH3:22]>C(O)C>[CH2:21]([O:23][NH:24][C:1](=[C:6]1[C:11](=[O:12])[CH:10]([CH3:13])[CH:9]([CH2:14][CH:15]([S:17][CH2:18][CH3:19])[CH3:16])[CH2:8][C:7]1=[O:20])[CH2:2][CH2:3][CH3:4])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Into 10 ml of ethanol, 2.97 g of 2-butyryl-5-(2-ethylthiopropyl)-4-methylcyclohexane-1,3-dione was dissolved and 0.81 g of ethoxyamine was dropped thereto at 0° C. and the resulting solution was stirred at room temperature for 3 hours. After pouring the reaction solution into ice-cold water, the mixture was extracted with chloroform. The chloroform solution was washed with water and extracted with 1N-sodium hydroxide solution. The sodium hydroxide solution was acidified with 1N-hydrochloric acid and the acidified mixture was extracted with chloroform. The chloroform solution was washed with water and dried over anhydrous magnesium sulfate. The removal of chloroform from said chloroform solution by distillation under reduced pressure gave 3.0 g of the desired product as yellow oily material.

Workup

additionAfter pouring the reaction solution into ice-cold water
extractionthe mixture was extracted with chloroform
washThe chloroform solution was washed with water
extractionextracted with 1N-sodium hydroxide solution
extractionthe acidified mixture was extracted with chloroform
washThe chloroform solution was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe removal of chloroform
distillationby distillation under reduced pressure

Sources & evidence

ORD record: ord-cb08fc56a8a6453ea54fc589ea838b11
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04579971

Reaction notes

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