Dimethylformamide → HCID 178462845, compound

HRID 236331Notes

Reaction equation

HRID 236331 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]2[CH:17]=[C:18]([C:20]#[N:21])[CH:19]=[C:9]2[C:8]1=[O:22])[CH3:6].[Cl-].[NH4+].CN(C)C=O>O>[CH2:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]2[CH:17]=[C:18]([C:20]3[NH:21][N:3]=[N:2][N:1]=3)[CH:19]=[C:9]2[C:8]1=[O:22])[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13770490HCID 13770490, compound

Product 1

HCID 178462845HCID 178462845, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.48 g (7.4 mmole) of sodium azide were added to a suspension of 1.3 g (5.5 mmole) of the product of Step B, 0.425 g (8.0 mmole) of ammonium chloride and 50 ml of dimethylformamide and the mixture was stirred at 130°-140° C. for 12 hours and was then cooled. 200 ml of water were added thereto and the mixture was filtered. The recovered product was crystallized from a methanol-ethyl acetate mixture to obtain 0.74 g (48% yield) of 5-ethyl-2-(1H-tetrazol-5-yl)-pyrrolo-[1,2-a]-quinoxaline-4(5H)-one in the form of off-white crystals melting at 295°-297° C. with decomposition.

Workup

  1. temperaturewas then cooled
  2. filtrationthe mixture was filtered
  3. customThe recovered product was crystallized from a methanol-ethyl acetate mixture

Sources & evidence

ORD record
ord-2e2da5091c50476cab409cf00e1074b5
Source dataset
uspto-grants-1987_02
Patent number
US04644002

Reaction notes

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