1,1'-Carbonyldiimidazole → HCID 178522724, compound

HRID 2057471Notes

Reaction equation

HRID 2057471 reaction equation
[O:1]=[C:2]1[C:7]([C:8](O)=[O:9])=[CH:6][NH:5][C:4]2[C:11](=[O:19])[O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:3]1=2.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:33][C:34]1[NH:38][N:37]=[N:36][N:35]=1>CN(C)C=O>[O:1]=[C:2]1[C:7]([C:8]([NH:33][C:34]2[NH:38][N:37]=[N:36][N:35]=2)=[O:9])=[CH:6][NH:5][C:4]2[C:11](=[O:19])[O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:3]1=2

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 12736945HCID 12736945, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178522724HCID 178522724, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,5-dihydro-1,5-dioxo-4H-1-benzopyrano[3,4-b]pyridine-2-carboxylic acid (2.57 g, 0.01 mole) and 1,1'-carbonyldiimidazole (1.95 g, 0.012 mole) in dimethylformamide is heated at 100 for 60 minutes under nitrogen. The reaction mixture is cooled and stirred at room temperature for 15 minutes. 5-Aminotetrazole monohydrate (1.24 g, 0.012 mole) is added and the resulting mixture is heated at 100 for 60 minutes, cooled, and filtered. The product is recrystallized from dimethylformamide to give white crystals (1.1 g, 34%), m.p. above 300.

Workup

  1. temperatureis heated at 100 for 60 minutes under nitrogen
  2. temperatureThe reaction mixture is cooled
  3. temperaturethe resulting mixture is heated at 100 for 60 minutes
  4. temperaturecooled
  5. filtrationfiltered
  6. customThe product is recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-6af3dab100984da392b20c03b4d6d66d
Source dataset
uspto-grants-1980_07
Patent number
US04210758

Reaction notes

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