Dimethylformamide → HCID 57664025, compound

HRID 1510252Notes

Reaction equation

HRID 1510252 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[N:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1>ClCCl.O.N1C=CC=CC=1>[N:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:6]([C:2]3[NH:1][CH:5]=[CH:4][CH:3]=3)=[O:8])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 12473Pyrrole-2-Carboxylic AcidHCID 65578Oxalyl chlorideHCID 15126544-(Pyridin-4-yl)aniline

Product 1

HCID 57664025HCID 57664025, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1H-pyrrole-2-carboxylic acid (45.0 mg) in dichloromethane (1.8 mL) were added oxalyl chloride (0.053 mL) and one-drop of N,N-dimethylformamide at 0° C. After 15 minutes, [4-(4-pyridinyl)phenyl]amine (68.9 mg) and pyridine (0.131 mL) were added to the mixture at 0° C. and the resulting mixture was stirred at ambient temperature overnight. Water (3 mL) was added to the mixture. The precipitate was collected by filtration and washed with water (2 mL) to afford N-[4-(4-pyridinyl)phenyl]-1H-pyrrole-2-carboxamide (65.2 mg) as white crystals.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water (2 mL)

Sources & evidence

ORD record
ord-d58fbda1a01a4e5bb04d4d556f2ef8b3
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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