Ammonium Chloride → HCID 178441092, compound

HRID 2081285Notes

Reaction equation

HRID 2081285 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:32][N:31]=[N:30][N:24]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19799556HCID 19799556, compound

Product 1

HCID 178441092HCID 178441092, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]pyrazole-3-carboxylate (730 mg) in dimethylformamide (10 ml) were added sodium azide (1.3 g) and ammonium chloride (1.07 g) and the mixture was stirred at 110°-115° C. for 72 hours. Insoluble materials were filtered off, and the filtrate was concentrated to dryness. To the residue were added 0.5 N-hydrochloric acid (40 ml) and ether (100 ml) for partitioning, and the organic layer was washed with water, dried, and concentrated to dryness. The residue was purified by column chromatography on silica gel to give the desired product as a colorless powder (470 mg, 58%).

Workup

  1. filtrationInsoluble materials were filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. additionTo the residue were added 0.5 N-hydrochloric acid (40 ml) and ether (100 ml)
  4. customfor partitioning
  5. washthe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-af71e082d0e340b5ac9808d9c99382b1
Source dataset
uspto-grants-1993_02
Patent number
US05183899

Reaction notes

Loading…