HCID 21426418, compound → HCID 178487975, compound

HRID 258666Notes

Reaction equation

HRID 258666 reaction equation
[Cl:1][C:2]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[C:4]([C:5](O)=[O:6])[CH:3]=1.[NH2:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1>CN(C)C=O>[Cl:1][C:2]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[C:4]([C:5]([NH:17][C:18]2[NH:22][N:21]=[N:20][N:19]=2)=[O:6])[CH:3]=1

Participants

4

Reactant 2

HCID 21426418HCID 21426418, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178487975HCID 178487975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N'-Carbonyldiimidazole (13.3 g) and 4-chloro-6-methoxyquinaldic acid (19.5 g) in dimethylformamide (100 ml) were stirred at room temperature for 2 hours. 5-Aminotetrazole was added and the mixture was stirred for 16 hours at room temperature. The solution was concentrated to 50 ml. and cooled. The solid was collected and dissolved in a warm mixture of dimethylformamide (50 ml) and dimethylaminoethanol (10 ml). The solid which crystallised was dissolved in water and the solution was acidified to pH 1 with dilute hydrochloric acid. The solid which separated was collected, washed with water and dried, m.p. 300° (d).

Workup

  1. concentrationThe solution was concentrated to 50 ml
  2. temperatureand cooled
  3. customThe solid was collected
  4. dissolutiondissolved in a warm mixture of dimethylformamide (50 ml) and dimethylaminoethanol (10 ml)
  5. customThe solid which crystallised
  6. dissolutionwas dissolved in water
  7. customThe solid which separated
  8. customwas collected
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-3fd35dc66b144875b174f0be99812af8
Source dataset
uspto-grants-1977_07
Patent number
US04034075

Reaction notes

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