Methyl Isobutyl Ketone → N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea

HRID 265732Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N:9]([CH2:12][C:13]([Cl:15])=[CH2:14])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.C(C(C)=O)C(C)C.[NH4+]=[S:26]>O>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([N:9]([CH2:12][C:13]([Cl:15])=[CH2:14])[C:10]([NH2:11])=[S:26])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)cyanamide (168.67 g), methyl isobutyl ketone ((674.70 g) and ammonium sulfide solution, yellow (518.77 g) having an S content of 6% was stirred at 50° C. for 9 hours. After cooling to 20° C., water (1774.70 g) was poured into the reaction mixture, which was then shaken and fractionated with a separatory funnel. The water layer was extracted twice with methyl isobutyl ketone (53.72 g×2). The combined methyl isobutyl ketone layer was washed with water (81.05 g) to give a methyl isobutyl ketone solution (938.58 g) of N-(3-(trifluoromethyl)phenyl)-N-(2-chloro-2-propenyl)thiourea.

Workup

temperatureAfter cooling to 20° C.
stirringwas then shaken
customfractionated with a separatory funnel
extractionThe water layer was extracted twice with methyl isobutyl ketone (53.72 g×2)
washThe combined methyl isobutyl ketone layer was washed with water (81.05 g)

Sources & evidence

ORD record: ord-9db34c6add5347c8928075b1a44c3760
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648533

Reaction notes

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