Dimethylformamide → HCID 22622781, compound

HRID 840285Notes

Reaction equation

HRID 840285 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([F:11])([F:10])[F:9])[C:4]([C:12]([OH:14])=O)=[CH:3]1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[C:26]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]([NH2:32])=[CH:28][CH:29]=[CH:30][CH:31]=1>C(Cl)Cl.C(N(CC)CC)C>[C:26]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:12]([C:4]1[C:5]([C:8]([F:9])([F:10])[F:11])=[C:6]([CH3:7])[N:2]([CH3:1])[CH:3]=1)=[O:14]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 70152-AminobiphenylHCID 65578Oxalyl chlorideHCID 22622778HCID 22622778, compound

Product 1

HCID 22622781HCID 22622781, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A solution of 1,5-dimethyl-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)-1,5-dimethyl-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-faf7e4e0618943a38ff9b169c22b396f
Source dataset
uspto-grants-2002_04
Patent number
US06365620B2

Reaction notes

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