1,1'-Carbonyldiimidazole → HCID 178466022, compound

HRID 267511Notes

Reaction equation

HRID 267511 reaction equation
[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:17])[C:9]([C:14]([OH:16])=O)=[CH:10][NH:11]2)=[CH:6][CH:5]=1)[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:30][C:31]1[NH:35][N:34]=[N:33][N:32]=1>CN(C)C=O>[CH2:1]([O:3][C:4]1[N:13]=[C:12]2[C:7]([C:8](=[O:17])[C:9]([C:14]([NH:30][C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[O:16])=[CH:10][NH:11]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 21435022HCID 21435022, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178466022HCID 178466022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Ethoxy-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (1.9 g) and N,N-carbonyldiimidazole (2 g) in dimethylformamide (50 ml) were stirred and heated at 100° for 4 hours. 5-Amino-1H-tetrazole (2.1 g) was added and the mixture stirred and heated at 100° for 30 minutes, and cooled. The solid was collected and dissolved in hot (60°) dilute sodium hydroxide and the solution was neutralised (pH 7) with dilulte hydrochloric acid. The solid was collected, washed with water and dried, m.p. above 319° (d), (75 %).

Workup

  1. temperatureheated at 100° for 4 hours
  2. temperatureheated at 100° for 30 minutes
  3. temperaturecooled
  4. customThe solid was collected
  5. dissolutiondissolved in hot (60°) dilute sodium hydroxide
  6. customThe solid was collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-e0b005dda47646d88ad47b137fc192d4
Source dataset
uspto-grants-1976_03
Patent number
US03943141

Reaction notes

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