Ammonium Chloride → HCID 178458295, compound

HRID 363369Notes

Reaction equation

HRID 363369 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([OH:9])[N:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][CH2:18][CH3:19])[N:4]=1)#[N:2].[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH2:17]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:5]1[NH:6][C:7](=[O:9])[CH:8]=[C:3]([C:1]2[NH:22][N:21]=[N:20][N:2]=2)[N:4]=1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 178458305HCID 178458305, compound

Product 1

HCID 178458295HCID 178458295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4-cyano-6-hydroxy-2-(2-propoxyphenyl)pyrimidine (325 mg), sodium azide (91 mg) and ammonium chloride (75 mg) in dimethylformamide (15 ml) was heated at 125° C. for 5 hours. Most of the dimethylformamide was removed under reduced pressure and water added to the oily residue which solidified. The mixture was cooled and the solid was collected, washed with water and recrystallized from glacial acetic acid to yield the title compound, 174 mg, m.p. 219°-221° C.

Workup

  1. customMost of the dimethylformamide was removed under reduced pressure and water
  2. additionadded to the oily residue which
  3. temperatureThe mixture was cooled
  4. customthe solid was collected
  5. washwashed with water
  6. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-d70547f8740a4a0d9ea50c5055b96988
Source dataset
uspto-grants-1999_02
Patent number
US05874440

Reaction notes

Loading…