Chloroacetonitrile → HCID 12895385, compound

HRID 442397Notes

Reaction equation

Cl[C:2]1[C:3]([N+:20]([O-:22])=[O:21])=[C:4]([C:10]([N+:17]([O-:19])=[O:18])=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[N:5]([CH2:8][CH3:9])[CH2:6][CH3:7].O.O.O.O.O.O.O.O.O.[S-2:32].[Na+].[Na+].Cl[CH2:36][C:37]#[N:38]>CS(C)=O>[C:37]([CH2:36][S:32][C:2]1[C:3]([N+:20]([O-:22])=[O:21])=[C:4]([C:10]([N+:17]([O-:19])=[O:18])=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[N:5]([CH2:8][CH3:9])[CH2:6][CH3:7])#[N:38]

Participants

Conditions

Temperature: 0 °C

Procedure

The preparation of a compound bearing a cyanomethylthio group in the 3-position is conveniently carried out using an inert solvent such as dimethylsulfoxide. Thus, a mixture of 3-chloro-N,N-diethyl-2,6-dinitro-4-trifluoromethylaniline and sodium sulfide nonahydrate in a suitable solvent such as dimethylsulfoxide is stirred for a period of time at about 0° C. There is then added chloroacetonitrile and the reaction mixture is stirred overnight at ambient room temperature. The reaction mixture is poured over ice and extracted with ether. The ether is evaporated and the residue recrystallized from a suitable solvent such as ethanol to yield in this case 3-cyanomethylthio-N,N-diethyl-2,6-dinitro-4-trifluoromethylaniline having a melting point of about 77°-79° C. The structure is confirmed by NMR spectrum.

Workup

customThe preparation of a compound
additionThe reaction mixture is poured over ice
extractionextracted with ether
customThe ether is evaporated
customthe residue recrystallized from a suitable solvent such as ethanol

Sources & evidence

ORD record: ord-402fcfeeee704e64b2285d54cf29a4f2
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04045466

Reaction notes

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