Triethylamine → 4-(4-Imino-2-thioxo-1-(4-methylphenyl)-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile

HRID 244983

Reaction equation

HRID 244983 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]1[CH:29]=[CH:28][C:27]([NH:30][C:31]2([C:37]#[N:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1.ClCCl.CC(C)=O>C1COCC1>[NH:38]=[C:37]1[C:31]2([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[N:30]([C:27]2[CH:26]=[CH:25][C:24]([CH3:23])=[CH:29][CH:28]=2)[C:9](=[S:10])[N:8]1[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:20])([F:22])[F:21])[CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 598390991-p-Tolylaminocyclohexanecarbonitrile

Product 1

HCID 866098544-(4-Imino-2-thioxo-1-(4-methylphenyl)-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrileYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.05 g, 0.5 mmol) was added to a solution of 1a (0.228 g, 1 mmol) and 9a (0.214 g, 1 mmol) in dry THF (2 ml). The reaction mixture was stirred at room temperature for 2 days and then concentrated to yield a dark residue which was subjected to flash chromatography (dichloromethane/acetone, 95:5) to afford 4-(4-imino-2-thioxo-1-(4-methylphenyl)-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile, 9b (0.035 g, 0.08 mmol, 8%).

Workup

  1. concentrationconcentrated
  2. customto yield a dark residue which

Sources & evidence

ORD record
ord-502f5d41c4a84ab9a2d22f622a5107c6
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Linked notes

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