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

HRID 2233666Notes

Reaction equation

HRID 2233666 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].[OH:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([CH3:35])([CH3:34])[C:32]#[N:33])=[CH:26][CH:25]=1.ClCCl.CC(C)=O>C1COCC1>[OH:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[C:31]([CH3:34])([CH3:35])[C:32](=[NH:33])[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:28][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 3502692-(4-Hydroxyphenylamino)-2-methylpropanenitrileHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 21584124Propan-2-one--dichloromethane (1/1)

Product 1

HCID 866098534-[3-(4-Hydroxyphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrileYield 34%

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 3a (0.352 g, 2 mmol) in dry THF (5 ml). The reaction mixture was stirred at 0° C. for 48 h and then concentrated to yield a dark residue which was subjected to flash chromatography (dichloromethane/acetone, 85:15) to afford 4-[3-(4-hydroxyphenyl)-5-imino-4,4-dimethyl-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile, 3b (0.274 g, 0.68 mmol, 34%).

Workup

  1. concentrationconcentrated
  2. customto yield a dark residue which

Sources & evidence

ORD record
ord-4ef9acb4197a40139591727e6520ab86
Source dataset
uspto-grants-2010_05
Patent number
US07709517B2

Reaction notes

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