p-Toluenesulfonic acid → HCID 68538382, compound

HRID 1993674Notes

Reaction equation

HRID 1993674 reaction equation
O=C(C1(C(F)(F)F)CC1)CC#[N:5].[C:13](=[N:26][NH:27][C:28]1[CH:29]=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=1)([C:20]1[CH:25]=CC=[CH:22][CH:21]=1)[C:14]1[CH:19]=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:25][C:20]1([C:13]2[CH:14]=[C:19]([NH2:5])[N:27]([C:28]3[CH:29]=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[N:26]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11300678HCID 11300678, compoundHCID 668764113-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

Product 1

HCID 68538382HCID 68538382, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 3-Oxo-3-(1-trifluoromethyl-cyclopropyl)-propionitrile (2.66 g, 15.0 mmol), N-benzhydrylidene-N′-(6-methyl-pyridin-3-yl)-hydrazine (TL, 2002, 43, 2171-2173) (4.31 g, 15.0 mmol), and p-tolylsulfonic acid (14.29 g, 75.0 mmol) in ethanol (85 mL) at 90° C. in a sealed tube for 18 hours. After removal of the solvent, subject residue to silica gel chromatography eluting with 0-5% methanol in dichloromethane to give a brown solid (2.29 g, 54% yield). MS(ES+): m/z=283.2 [M+H].

Workup

  1. temperatureHeat
  2. customAfter removal of the solvent
  3. washeluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-047e225ab48a43d7a018e008e7408721
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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