Dimethylformamide → HCID 17974869, compound

HRID 227229Notes

Reaction equation

HRID 227229 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]([F:19])([F:18])[C:9]1[C:14]([C:15]([OH:17])=O)=[CH:13][N:12]=[CH:11][CH:10]=1.CN(C)C=O.Br.[CH2:26]([N:33]1[C:37](=[NH:38])[S:36][CH:35]=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH2:26]([N:33]1[C:37](=[N:38][C:15]([C:14]2[CH:13]=[N:12][CH:11]=[CH:10][C:9]=2[C:8]([F:7])([F:19])[F:18])=[O:17])[S:36][CH:35]=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 17974866HCID 17974866, compound

Product 1

HCID 17974869HCID 17974869, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Oxalyl chloride (0.6 ml) was added to a suspension of 4-trifluoromethylnicotinic acid (1 g) and a catalytic amount of N,N-dimethylformamide in dichloromethane, and stirred at 20° C. for 1 hour. 4-Benzyl-5-imino-1,3,4-thiadiazoline hydrobromide (1.44 g) was added under ice cooling, and was stirred at 20° C. for 1 hour. The mixture was then washed (water), dried (magnesium sulfate), evaporated and the residue recrystallized (ethanol) to give 4-benzyl-5-(4-trifluoromethyl-3-pyridylcarbonyl)imino-1,3,4-thiadiazoline (0.3 g, Compound E-39).

Workup

  1. washThe mixture was then washed (water)
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated
  4. customthe residue recrystallized (ethanol)

Sources & evidence

ORD record
ord-689ef9abdc8440f980336cf9de2323e4
Source dataset
uspto-grants-2009_07
Patent number
US07560456B2

Reaction notes

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