Water → HCID 54522751, compound

HRID 48133

Reaction equation

[OH:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:4]#[N:5].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.O>O1CCCC1>[CH3:16][S:17]([O:1][N:2]=[C:3]([CH:6]=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)[C:4]#[N:5])(=[O:19])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

2-hydroxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile (1.8 g; 9 mmol) is dissolved in 15 ml of anhydrous tetrahydrofuran, and cooled to 0° C. Methanesulfonyl chloride (0.93 ml, 0.012 mol) is added at once, followed by triethylamine (2 ml, 0.015 mol) dropwise over 20 min, keeping the temperature of the mixture below 5° C. The mixture is then stirred at 2° C. for 1 h 15 min, and poured into 200 ml of iced water. The suspension is extracted with ethyl acetate, the organic extract is washed neutral with water, then with brine, and dried over magnesium sulfate. Rotary evaporation of the solvent and recrystallization from 80 ml of ethanol yields 2-methylsulfonyloxyimino-4-(4-methoxy-phenyl)-but-3-enenitrile (1.02 g; 41%) as light yellow hair-like crystals, mp 147-152° C. (dec). 1H-NMR reveals the presence of only one isomer.

Workup

customthe temperature of the mixture below 5° C
extractionThe suspension is extracted with ethyl acetate
extractionthe organic extract
washis washed neutral with water
dry with materialwith brine, and dried over magnesium sulfate
customRotary evaporation of the solvent and recrystallization from 80 ml of ethanol

Sources & evidence

ORD record: ord-212d808d04a24f93b79c9b42fc64dcf5
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703182B1

Linked notes

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