Triethylamine → 4-(4-Imino-2-thioxo-1,3-diazaspiro[4.4]non-3-yl)-2-trifluoromethylbenzonitrile

HRID 244994

Reaction equation

HRID 244994 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].[NH2:23][C:24]1([C:29]#[N:30])[CH2:28][CH2:27][CH2:26][CH2:25]1.ClCCl.CC(C)=O>C1COCC1>[NH:30]=[C:29]1[C:24]2([CH2:28][CH2:27][CH2:26][CH2:25]2)[NH:23][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 21068971-AminocyclopentanecarbonitrileHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 21584124Propan-2-one--dichloromethane (1/1)

Product 1

HCID 866098554-(4-Imino-2-thioxo-1,3-diazaspiro[4.4]non-3-yl)-2-trifluoromethylbenzonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.101 g, 0.1 mmol) was added to a solution of 1a (0.684 g, 3 mmol) and 24a (0.33 g, 3 mmol) in dry THF (5 ml). The reaction mixture was stirred at room temperature for 5 h and then concentrated to yield a brown residue which was subjected to flash chromatography (dichloromethane/acetone, 93:7) to afford 24b (0.741 g, 2.19 mmol, 73%).

Workup

  1. concentrationconcentrated
  2. customto yield a brown residue which

Sources & evidence

ORD record
ord-c9ed0411a26f40f780b961b7f677fc1a
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Linked notes

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