Acetonitrile → 4-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene

HRID 258762Notes

Reaction equation

[S-:1][C:2]#[N:3].[K+].C(#N)C.Cl[C:9]([O:11][CH3:12])=[O:10].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:21][CH3:22])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]>O>[CH2:21]([S:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:2]([NH:3][C:9]([O:11][CH3:12])=[O:10])=[S:1])=[C:15]([N+:23]([O-:25])=[O:24])[CH:16]=1)[CH3:22]

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of dry potassium thiocyanate (25.65 g.) and acetonitrile (320 ml.) was cooled to 10° C. and treated during 5 minutes with methyl chloroformate (25.0 g.). The mixture was stirred at room temperature for 2 hours. 1-Amino-4-ethylthio-2-nitrobenzene (22.45 g.) was then added to the mixture at 10°-15° C. The suspension was stirred for 3 hours at room temperature and allowed to stand overnight. It was then poured into water (1.6 liters) and the solid which precipitated was filtered off, washed with water and recrystallised from a mixture of methanol and ethanol, to give 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene (14.0 g.), m.p. 152° C.

Workup

stirringThe suspension was stirred for 3 hours at room temperature
waitto stand overnight
customthe solid which precipitated
filtrationwas filtered off
washwashed with water
customrecrystallised from a mixture of methanol and ethanol

Sources & evidence

ORD record: ord-c37ed3ac3f494bd9bfe7ce054493466d
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04034107

Reaction notes

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