Triethylamine → 4-[3-(4-Methylphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

HRID 244971

Reaction equation

HRID 244971 reaction equation
C(N(CC)CC)C.[N:8]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=1)=[C:9]=[S:10].[CH3:23][C:24]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)([CH3:27])[C:25]#[N:26].ClCCl.CC(C)=O>C1COCC1>[CH3:35][C:32]1[CH:31]=[CH:30][C:29]([N:28]2[C:24]([CH3:23])([CH3:27])[C:25](=[NH:26])[N:8]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:20])([F:22])[F:21])[CH:12]=3)[C:9]2=[S:10])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 212392432-Methyl-2-[(4-methylphenyl)amino]propanenitrileHCID 21584124Propan-2-one--dichloromethane (1/1)

Product 1

HCID 159518184-[3-(4-Methylphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.101 g, 1 mmol) was added to a solution of 1a (0.456 g, 2 mmol) and 5a (0.348 g, 2 mmol) in dry THF (3 ml). The reaction mixture was stirred at 0° C. for 2 days and then concentrated to yield a dark residue which was subjected to flash chromatography (dichloromethane/acetone, 95:5) to afford 4-[3-(4-methylphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile, 5b (0.136 g, 0.34 mmol, 17%).

Workup

  1. concentrationconcentrated
  2. customto yield a dark residue which

Sources & evidence

ORD record
ord-672fc72e07f74006bd18aeb2002a59bf
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Linked notes

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