Ethanethiol → 4-(2,4-Dichlorophenyl)-2-ethylthiobenzonitrile

HRID 25286Notes

Reaction equation

[H-].[Na+].[CH2:3]([SH:5])[CH3:4].[H][H].F[C:9]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]>CN(C)C=O>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:15]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([S:5][CH2:3][CH3:4])[CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.12 g (3.0 mmol) of 60% sodium hydride was stirred in 30 ml of N,N-dimethylformamide at room temperature while 0.2 g (3.2 mmol) of ethanethiol was added dropwise. After generation of hydrogen was over, 0.7 g (2.6 mmol) of 2-fluoro-4-(2,4-dichlorophenyl)benzonitrile was added, and the reaction mixture was stirred at 60° C. for 6 hours. The reaction mixture was poured into about 100 ml of ice-cold water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.7 g of 4-(2,4-dichlorophenyl)-2-ethylthiobenzonitrile (yield 88.0%) as pale yellow crystals (m.p. 89-92° C.).

Workup

additionwas added dropwise
additionwas added
extractionextracted with 50 ml of ethyl acetate twice
washThe ethyl acetate layer was washed with 50 ml of water twice
dry with materialdried over anhydrous magnesium sulfate
distillationthe ethyl acetate was distilled off under reduced pressure
customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record: ord-40d95e66658444e282e4585cc3250eed
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858639B2

Reaction notes

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