Hydrochloric Acid → HCID 178518601, compound

HRID 1709230Notes

Reaction equation

HRID 1709230 reaction equation
[C:1]([CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[C:5]1=[O:15])#[N:2].[Cl-].[NH4+].[N-:18]=[N+:19]=[N-:20].[Na+].Cl>CN(C)C=O>[NH:18]1[C:1]([CH2:3][N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6](=[O:14])[C:5]2=[O:15])=[N:2][N:20]=[N:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19827841HCID 19827841, compound

Product 1

HCID 178518601HCID 178518601, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-cyanomethylquinoxaline-2,3(1H,4H)-dione (0.60 g, 3.0 mmol) in 10 ml of N,N-dimethylformamide was added ammonium chloride (0.18 g, 3.4 mmol) and sodium azide (0.22 g, 3.4 mmol), and the mixture was stirred on an oil bath at 100° C. for 4 h. The mixture was cooled to room temperature and 25 ml of 1M hydrochloric acid was added. The precipitated solid was isolated by filtration and washed with water, ethanol and ether to give 0.71 g (97%) of the title compound. M.p. 320.4° C. (DSC); IR (KBr): 1700, 1650, 1600 cm-1 ; 1H-NMR (DMSO-d6): 5.62 (s, 2H, CH2), 7.08 (s, 4H, ArH), 12.2 (broad s, 1H, NH; only one exchangeable proton could be seen); MS (m/z): 244 (M+, 49%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe precipitated solid was isolated by filtration
  3. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-c25aee37698b4ae29c924f77bf2d2d69
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Reaction notes

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