1,1'-Carbonyldiimidazole → HCID 178522694, compound

HRID 2049754Notes

Reaction equation

HRID 2049754 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8](O)=[O:9])[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[CH:7]=[C:6]([C:8]([NH:33][C:34]2[NH:38][N:37]=[N:36][N:35]=2)=[O:9])[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 21786916HCID 21786916, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178522694HCID 178522694, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,5-dihydro-1,5-dioxo-4H-1-benzopyrano[3,4-b]pyridine-3-carboxylic acid (2.57 g, 0.01 mole) and 1,1'-carbonyldiimidazole (3.24 g, 0.02 mole) in dimethylformamide (50 ml) is heated at 100 for 60 minutes under nitrogen. The reaction mixture is cooled. 5-aminotetrazole monohydrate (1.03 g, 0.01 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 (1.51 g, 39%) mp 265-270. The product crystallizes as a 1:1 salt or complex with 1H-imidazole.

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-5cef7129d97c45a1857427ac9526be63
Source dataset
uspto-grants-1980_04
Patent number
US04198511

Reaction notes

Loading…