Thionyl Chloride → n-(3,5-Bis trifluoromethyl-benzyl)-n-cyclopropyl-4-o-tolyl-nicotinamide

HRID 379368Notes

Reaction equation

HRID 379368 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[F:21][C:22]([F:39])([F:38])[C:23]1[CH:24]=[C:25]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:26][NH:27][CH:28]1[CH2:30][CH2:29]1>ClCCl.CN(C)C=O>[F:21][C:22]([F:38])([F:39])[C:23]1[CH:24]=[C:25]([CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=1)[CH2:26][N:27]([CH:28]1[CH2:29][CH2:30]1)[C:13](=[O:15])[C:12]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:16])=[CH:8][CH:9]=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 158874064-(2-Methylphenyl)nicotinic acidHCID 15887407(3,5-Bistrifluoromethylbenzyl)cyclopropylamine

Product 1

HCID 9806536n-(3,5-Bis trifluoromethyl-benzyl)-n-cyclopropyl-4-o-tolyl-nicotinamideYield 58.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 106 mg (0.5 mmol) 4-o-tolyl-nicotinic acid in 5 ml dichloromethane and 2 drops N,N-dimethylformamide was stirred with 0.1 ml (1.4 mmol) thionyl chloride for 1.5 h at room temperature. The solvent was removed and the residue was taken up in 5 ml dichloromethane and 0.3 ml triethylamine. After the addition of 155 mg (0.55 mmol) (3,5-bis-trifluoromethyl-benzyl)-cyclopropyl-amine the mixture was stirred at room temperature for 1 h and washed twice with water. The organic layer was dried (magnesium sulfate) and evaporated. The crude oil was subjected to column chromatography to give 140 mg (58%) of the title compound as an oil.

Workup

  1. customThe solvent was removed
  2. washwashed twice with water
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-5d5120a0398f4c2dbae2f4f6d6fdd56e
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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