1,1'-Carbonyldiimidazole → HCID 178522697, compound

HRID 1632200Notes

Reaction equation

HRID 1632200 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([CH: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>C(OCC)(=O)C>[NH:31]1[C:30]([NH:29][C:14]([C:2]2[N:3]=[C:4]3[CH:13]=[CH: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 12763992HCID 12763992, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178522697HCID 178522697, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

0.85 g (4 mmol) of imidazo-[1,2-a]-quinoline-2-carboxylic acid [prepared as in published French application No. 2,378,301] was heated at 160° C. in vacuo for one hour to remove water of crystallization and was then dissolved in 25 ml of dimethylformamide. The solution was stirred at 90° to 100° C. with 0.72 g (4.4 mmol) of carbonyldiimidazole and the mixture was stirred at 100° C. for 40 minutes to obtain a slight suspension. 0.375 g of anhydrous 5-amino-tetrazole were added to the mixture which was then stirred at 100° C. for 45 minutes and was then cooled to room temperature. 20 ml of ethyl acetate were added to the mixture and the mixture was cooled in ice and was filtered to obtain 1.12 g of N-(1H-tetrazol-5-yl)-imidazo-[1,2-a]-quinoline-2-carboxamide in the form of colorless crystals melting at 266°-268° C. after crystallization from dimethylformamide.

Workup

  1. customto remove
  2. customwater of crystallization
  3. dissolutionwas then dissolved in 25 ml of dimethylformamide
  4. customto obtain a slight suspension
  5. stirringwas then stirred at 100° C. for 45 minutes
  6. temperaturewas then cooled to room temperature
  7. temperaturethe mixture was cooled in ice
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-5f7c18e197464e9bb2a5c4c0db7098d5
Source dataset
uspto-grants-1984_10
Patent number
US04474784

Reaction notes

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