Hydrochloric Acid → HCID 178441097, compound

HRID 2081287Notes

Reaction equation

HRID 2081287 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]([OH:27])=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:30][N:29]=[N:28][N:24]=3)=[CH:15][CH:16]=2)[N:8]=[C:7]([C:25]([OH:27])=[O:26])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19799551HCID 19799551, compound

Product 1

HCID 178441097HCID 178441097, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]pyrazole-3-carboxylic acid (17.6 g), sodium azide (19.5 g), and ammonium chloride (13.4 g) were stirred in dimethylformamide (DMF) (140 ml) at 110°-120° C. for 5 days. The reaction mixture was poured into water (1.2 1), to which conc. HCl (35 ml) and ethyl acetate (700 ml) were added. The organic layer was washed with 0.1 N-HCl and water, dried, and concentrated under reduced pressure. To the residue was added ether, and the resultant crude crystals were recrystallized from ethyl acetate-ether to give colorless crystals (16.3 g, 83%).

Workup

  1. additionwere added
  2. washThe organic layer was washed with 0.1 N-HCl and water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added ether
  6. customthe resultant crude crystals were recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-1db7937dfcc4416290c6d19bf4c988a7
Source dataset
uspto-grants-1993_02
Patent number
US05183899

Reaction notes

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