1,1'-Carbonyldiimidazole → HCID 178492684, compound

HRID 1155697Notes

Reaction equation

HRID 1155697 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)[N:6]=[C:5]([C:18]([OH:20])=O)[CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:33][C:34]1[NH:38][N:37]=[N:36][N:35]=1>CN(C)C=O>[NH:35]1[C:34]([NH:33][C:18]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([C:9]3[CH:10]=[CH:11][C:12]([N:15]([CH3:16])[CH3:17])=[CH:13][CH:14]=3)[N:6]=2)=[O:20])=[N:38][N:37]=[N:36]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 12811067HCID 12811067, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178492684HCID 178492684, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxy-6-(4-dimethylaminophenyl)-2-pyridinecarboxylic acid (0.44 g) in dimethylformamide (6 ml) is added carbonyldiimidazole (0.29 g), and the mixture is agitated at room temperature for one hour. To the mixture is added 5-aminotetrazole (0.15 g), and the mixture is heated at 70° C. for one hour. After cooling, the reaction mixture is poured into ice-water. The resulting precipitates are collected by filtration and washed with water and ethanol to give N-(5-tetrazolyl)-4-methoxy-6-(4-dimethylaminophenyl)-2-pyridinecarboxamide (0.36 g). M.P. 261°-263° C. (recrystallized from dimethylformamide-ethanol)

Workup

  1. temperaturethe mixture is heated at 70° C. for one hour
  2. temperatureAfter cooling
  3. customThe resulting precipitates
  4. filtrationare collected by filtration
  5. washwashed with water and ethanol

Sources & evidence

ORD record
ord-bb29bd699f4044f5b8f234176a556261
Source dataset
uspto-grants-1982_06
Patent number
US04332809

Reaction notes

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