Triethylamine → 2-(Trifluoromethyl)benzonitrile

HRID 244986Notes

Reaction equation

HRID 244986 reaction equation
C(N(CC)CC)C.N([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=S.CC1C=CC(NC2(C#N)CCCCC2)=CC=1.ClCCl.CC(C)=O>C1COCC1>[F:20][C:19]([F:21])([F:22])[C:13]1[CH:12]=[CH:11][CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

6

Reactant 4

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

Product 1

HCID 679722-(Trifluoromethyl)benzonitrile

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 (0.228 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]undec-3-yl)-2-trifluoromethylbenzonitrile, 10b (0.036 g, 0.08 mmol, 8%).

Workup

  1. concentrationconcentrated
  2. customto yield a dark residue which

Sources & evidence

ORD record
ord-bb5d9e18cecc4e85869c1680e3a0b047
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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