1,1'-Carbonyldiimidazole → 5-chloro-1-methyl-N-cyclopropyl-1H-pyrazole-4-carboxamide

HRID 1731271

Reaction equation

HRID 1731271 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[N:18]([CH3:19])[N:17]=[CH:16][C:15]=1[C:20]([OH:22])=O.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>O1CCCC1>[Cl:13][C:14]1[N:18]([CH3:19])[N:17]=[CH:16][C:15]=1[C:20]([NH:26][CH:23]1[CH2:25][CH2:24]1)=[O:22]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 69828CyclopropylamineHCID 27357745-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 138219895-chloro-1-methyl-N-cyclopropyl-1H-pyrazole-4-carboxamideYield 116.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (3.6 grams, 0.022 mole) was added to a solution of 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid (2.4 grams, 0.015 mole) in 40 ml. of tetrahydrofuran, and the solution was stirred at room temperature for twenty minutes. Cyclopropylamine (1.3 grams, 0.022 mole) was then added and the reaction mixture was stirred at room temperature for sixteen hours. Solvent was removed in vacuo and the residue was taken up in 250 ml. of chloroform, washed with water, washed with saturated brine, and dried using sodium sulfate and filter paper. The product was recrystallized from toluene, yielding 3.5 grams of 5-chloro-1-methyl-N-cyclopropyl-1H-pyrazole-4-carboxamide, mp=105°-107° C.

Workup

  1. customSolvent was removed in vacuo
  2. washof chloroform, washed with water
  3. washwashed with saturated brine
  4. customdried
  5. filtrationfilter paper
  6. customThe product was recrystallized from toluene

Sources & evidence

ORD record
ord-d38bd1c3d665459f8a8ea4d2f94daa22
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Linked notes

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