HCID 21491300, compound → HCID 178525588, compound

HRID 1973377Notes

Reaction equation

HRID 1973377 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]([OH:18])=O)[C:7]1=[O:19])=[O:2].[NH2:20][C:21]1[NH:25][N:24]=[N:23][N:22]=1>O1CCCC1.CN(C)C=O>[CH:1]([O:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]([NH:20][C:21]2[NH:25][N:24]=[N:23][N:22]=2)=[O:18])[C:7]1=[O:19])=[O:2]

Participants

5

Reactant 2

HCID 21491300HCID 21491300, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178525588HCID 178525588, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4(2-Formyloxyethyl)-3,4-dihydro-3-oxo-2-quinoxalinecarboxylic acid (1 g) and N,N'-carbonyldiimidazole (0.6 g) in dry tetrahydrofuran (100 ml) were heated under reflux for 15 minutes. 5-Amino-1H-tetrazole (0.5 g) in dimethylformamide (5 ml) was added and the mixture was heated under reflux for 1 hour. The solid was collected and treated with aqueous hydrochloric acid (25 ml., 2N). It was filtered off, dried and crystallised from aqueous dimethylformamide. It had m.p. 240°-241° (d).

Workup

  1. temperatureunder reflux for 15 minutes
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customThe solid was collected
  5. additiontreated with aqueous hydrochloric acid (25 ml., 2N)
  6. filtrationIt was filtered off
  7. customdried
  8. customcrystallised from aqueous dimethylformamide

Sources & evidence

ORD record
ord-d6146b96f5fb4b73bb4695fcaad61807
Source dataset
uspto-grants-1976_12
Patent number
US03997535

Reaction notes

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