1,1'-Carbonyldiimidazole → HCID 178522698, compound

HRID 236320Notes

Reaction equation

HRID 236320 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([N:12]=[CH:13][C:4]2=[N:3][C:2]=1[C:14]([OH:16])=O)=[CH:10][CH:9]=[CH:8][CH:7]=3.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:29][C:30]1[NH:34][N:33]=[N:32][N:31]=1>CN(C)C=O>[NH:31]1[C:30]([NH:29][C:14]([C:2]2[N:3]=[C:4]3[CH:13]=[N:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]3[CH:1]=2)=[O:16])=[N:34][N:33]=[N:32]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 71146DazoquinastHCID 178509299HCID 178509299, compound

Product 1

HCID 178522698HCID 178522698, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 0.8 g of imidazo-[1,2-a]-quinoxaline-2-carboxylic acid, 0.7 g of carbonyldiimidazole and 40 ml of dimethylformamide was stirred at 90° C. for 30 minutes and 0.35 g of anhydrous 5-amino-tetrazole were added to the resulting clear orange solution. The mixture was stirred at 90° C. for one hour and was cooled in a refrigerator. The mixture was filtered and the recovered product was washed well with ethyl acetate and dried in vacuo to obtain 1.17 g of N-(1H-tetrazol-5-yl)-imidazo-[1,2-a]-quinoxaline-2-carboxamide which after crystallization from dimethylformamide was a white crystalline solid melting at 280°-281° C. with decomposition.

Workup

  1. temperaturewas cooled in a refrigerator
  2. filtrationThe mixture was filtered
  3. washthe recovered product was washed well with ethyl acetate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7afb8df07d714e3b946d48984091c7ea
Source dataset
uspto-grants-1987_02
Patent number
US04644002

Reaction notes

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