1,1'-Carbonyldiimidazole → HCID 178521918, compound

HRID 1588787Notes

Reaction equation

HRID 1588787 reaction equation
[F:1][CH:2]([F:11])[C:3]1[C:7]([C:8](O)=[O:9])=[CH:6][NH:5][N:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:24]1([C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[NH2:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH:24]1([C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[NH:32][C:8]([C:7]2[C:3]([CH:2]([F:11])[F:1])=[N:4][NH:5][CH:6]=2)=[O:9])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4078992-CyclohexylbenzenamineHCID 178524804HCID 178524804, compound

Product 1

HCID 178521918HCID 178521918, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (2.0 g) and 1,1'-carbonyldiimidazole (2.0 g) were mixed in THF (20mL, anhydrous) and stirred for 1 h. 2-Cyclohexylaniline (2.2 g) was added, and the contents were heated at reflux for 2 h. After cooling to RT, the contents were concentrated in vacuo leaving a foam (3.7 g). The foam was chromatographed on silica gel (Waters Prep 500) eluting with EtOAc and hexanes to give the desired amide as a white foam (750 mg). The foam was crystallized from EtOAc /pentane to give the product as a white solid (510 mg).

Workup

  1. temperaturethe contents were heated
  2. temperatureat reflux for 2 h
  3. concentrationthe contents were concentrated in vacuo

Sources & evidence

ORD record
ord-11da2eefc2e24dc3a0c4cd109b9c27d3
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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