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

HRID 2379277Notes

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

Workup

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

Sources & evidence

ORD record: ord-7cd1eaaee2054133a0cbc33c57a65b64
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05360912

Reaction notes

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