1,1'-Carbonyldiimidazole → HCID 178513620, compound

HRID 2121358Notes

Reaction equation

HRID 2121358 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6](O)=O)[CH:3]=[N:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([NH2:26])=[O:25]>CN(C)C=O.N1C=CC=CC=1>[NH:2]1[CH:3]=[C:4]([C:6]2[NH:21][C:22]3[C:23]([C:24]([NH2:26])=[O:25])=[CH:27][CH:28]=[CH:29][C:30]=3[N:31]=2)[CH:5]=[N:1]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3015937Pyrazole-4-carboxylic acidHCID 104870292,3-Diaminobenzamide

Product 1

HCID 178513620HCID 178513620, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

35 0.56 g (5 mmol) of 4-pyrazolecarboxylic acid was stirred with 0.81 g (5 mmol) of carbonyldiimidazole in 20 ml of dimethylformamide at room temp. for 2 hours. 1.12 g (5 mmol) of 2,3-diaminobenzamide in 10 ml of pyridine were added. The reaction mixture was stirred at 50° C. for 2 hours. The reaction mixture was then concentrated in vacuo, and the residue was stirred with water. The precipitate was filtered off and dried in vacuo at 40° C. and then stirred in 10 ml of glacial acetic acid at 100° C. The residue after concentration in vacuo was stirred with saturated sodium bicarbonate solution. After filtration, the filtrate was concentrated with toluene in vacuo several times. The residue was stirred with tetrohydrofuran. Concentration in vacuo resulted in 150 mg of yellow powder.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. stirringthe residue was stirred with water
  3. filtrationThe precipitate was filtered off
  4. customdried in vacuo at 40° C.
  5. stirringstirred in 10 ml of glacial acetic acid at 100° C
  6. concentrationThe residue after concentration in vacuo
  7. stirringwas stirred with saturated sodium bicarbonate solution
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated with toluene in vacuo several times
  10. stirringThe residue was stirred with tetrohydrofuran
  11. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2f80afc0a1934015b899b30153608a13
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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