Dimethylformamide → 4-Trifluoromethylnicotinoyl chloride

HRID 1453815Notes

Reaction equation

HRID 1453815 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][C:8]([F:19])([F:18])[C:9]1C(C(O)=O)=[CH:13][N:12]=[CH:11][CH:10]=1.CN(C)C=O>ClCCl>[F:7][C:8]([F:19])([F:18])[C:9]1[C:1]([C:2]([Cl:4])=[O:3])=[CH:13][N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-

Product 1

HCID 117904654-Trifluoromethylnicotinoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (6.4 ml, 2M) was added to a suspension of 4-trifluoromethylnicotinic acid (2 g) and a catalytic amount of N,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1 hour to give a solution of 4-trifluoromethylnicotinic acid chloride. N,N-Ethylenethiourea (2.23 g) was added to sodium hydride (0.82 g, 60% dispersion in mineral oil) in tetrahydrofuran, and the mixture was stirred at 20° C. for 1 hour, and then added to the above solution of 4-trifluoromethylnicotinic acid chloride with ice bath cooling, then stirred at 20° C. for 1 hour. Ethyl acetate was added and the mixture washed with water, dried (magnesium sulfate), evaporated and the residue crystallized (ethanol) to give N-(4-trifluoromethyl-3-pyridylcarbonyl)-imidazolin-2-thione (1.35 g, Compound S-356).

Sources & evidence

ORD record
ord-e76f4efd84a84117b3a08fed3232cdaf
Source dataset
uspto-grants-2009_01
Patent number
US07476685B2

Reaction notes

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