Ammonium Chloride → HCID 178422376, compound

HRID 1439463Notes

Reaction equation

HRID 1439463 reaction equation
[C:1]([C:3]1[C:4](=[O:14])[O:5][C:6]2[C:11]([C:12]=1[CH3:13])=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:13][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:14])[C:3]=1[C:1]1[NH:17][N:16]=[N:15][N:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 2311464-Methyl-2-oxo-2H-chromene-3-carbonitrile

Product 1

HCID 178422376HCID 178422376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-cyano-4-methyl coumarin (7.94 g; 0.043 mole) in cimethylformamide (DMF) (45 ml) was added to a mixture of sodium azide (2.92 g; 0.044 mole) and ammonium chloride (2.36 g; 0.044 mole) and the stirred mixture heated on a steam bath for 24 hours. After removal of the solvent under reduced pressure, water (100 ml) was added and the solid filtered off. Acidification of the filtrate, and further aqueous extracts, afforded the title compound; m.p. (EtOH) 213°-4° C (Found: C, 57.58; H, 3.51; N, 24.41; C11H8N4O2 requires; C, 57.89; H, 3.53; N, 24.55%).

Workup

  1. temperaturethe stirred mixture heated on a steam bath for 24 hours
  2. customAfter removal of the solvent under reduced pressure, water (100 ml)
  3. additionwas added
  4. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-0ee7cc680d8a4bf292d524c40ab7193d
Source dataset
uspto-grants-1977_11
Patent number
US04059704

Reaction notes

Loading…