Dimethylformamide → N-(2-biphenylyl)-1-methyl-4-trifluoromethylpyrrol-3-carboxamide

HRID 840284Notes

Reaction equation

HRID 840284 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[C:4]([C:11]([OH:13])=O)=[CH:3]1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[C:25]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]([NH2:31])=[CH:27][CH:28]=[CH:29][CH:30]=1>C(Cl)Cl.C(N(CC)CC)C>[C:25]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:11]([C:4]1[C:5]([C:7]([F:10])([F:9])[F:8])=[CH:6][N:2]([CH3:1])[CH:3]=1)=[O:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 70152-AminobiphenylHCID 65578Oxalyl chlorideHCID 117887791-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 11244841N-(2-biphenylyl)-1-methyl-4-trifluoromethylpyrrol-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A solution of 1-methyl-4-trifluoromethylpyrrol-3-carboxylic acid (1.9 g) and oxalyl chloride (0.9 ml) in methylene chloride (20 ml) is stirred at room temperature in the presence of a catalytic amount of DMF. The solvent is evaporated under reduced pressure to give a crystalline solid. This solid is dissolved in methylene chloride (1 ml) and added to a solution of 2-biphenylamine (1.7 g) and triethylamine ( 4.2 ml) in methylene chloride (20 ml) at 0° C. The reaction mixture is stirred at room temperature for 2 hours. Evaporation of the solvent under reduced pressure, addition of water and filtering gives the N-(2-biphenylyl)-1-methyl-4-trifluoromethylpyrrol-3-carboxamide.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customto give a crystalline solid
  3. customEvaporation of the solvent
  4. additionunder reduced pressure, addition of water
  5. filtrationfiltering

Sources & evidence

ORD record
ord-193c3fb20b8044d4b9e1a22d4d97762d
Source dataset
uspto-grants-2002_04
Patent number
US06365620B2

Reaction notes

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