Acetyl chloride → N-[3-(trifluoromethyl)phenyl]-N-propargyl-N'-acetylthiourea

HRID 2379275Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Acetyl chloride (2.75 g) was mixed with acetonitrile (70 ml), and the mixture was cooled to 0° C. Then, potassium thiocyanate (3.75 g) was added thereto, and the mixture was stirred at room temperature for 6 hours. After cooling to 0° C. again, 3-trifluoromethyl-N-propargyl-aniline (7 g) was added thereto, and the mixture was stirred at room temperature for 3 hours. After the solvent was distilled off under reduced pressure, the residue was extracted with ethyl acetate (300 ml), and the extract was washed with water. The solvent was distilled off to give N-[3-(trifluoromethyl)phenyl]-N-propargyl-N'-acetylthiourea as crystallines (8 g). This identification was achieved by proton nuclear magnetic resonance (1H-NMR).

Workup

temperatureAfter cooling to 0° C. again
stirringthe mixture was stirred at room temperature for 3 hours
distillationAfter the solvent was distilled off under reduced pressure
extractionthe residue was extracted with ethyl acetate (300 ml)
washthe extract was washed with water
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-6ee135be352a40988d3d1c662e00b141
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05360912

Reaction notes

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