Sodium Hydroxide → HCID 178439463, compound

HRID 1357259Notes

Reaction equation

HRID 1357259 reaction equation
[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]#[N:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:34])[C:18]([C:20]1[CH:21]=[N:22][N:23]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]=1[CH2:25][CH2:26][CH3:27])=[O:19])=[CH:7]2.[N-:35]=[N+:36]=[N-:37].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:37][N:36]=[N:35][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:34])[C:18]([C:20]1[CH:21]=[N:22][N:23]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:24]=1[CH2:25][CH2:26][CH3:27])=[O:19])=[CH:7]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 12083570HCID 12083570, compound

Product 1

HCID 178439463HCID 178439463, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.30 g, 0.58 mmol), prepared in the previous step, sodium azide (0.113 g, 1.74 mmol) and ammonium chloride (0.093 g, 1.74 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for 6 h. By TLC the reaction was not complete. Sodium azide (0.113 g, 1.74 mmol) and ammonium chloride (0.093 g, 1.74 mmol) were added and the reaction was stirred under nitrogen at 100° C. for 6.5 h. The reaction was diluted with water, made basic by the addition of 1N NaOH and extracted five times with ethyl acetate. The combined organic extracts were acidified with 1N HCl and the solvent removed under reduced pressure. The residue was diluted with water and the solid that formed was collected by filtration and dried under reduced pressure to give the title compound (0.108 g, 33%) as a tan solid, mp 75-85° C.

Workup

  1. stirringthe reaction was stirred under nitrogen at 100° C. for 6.5 h
  2. extractionextracted five times with ethyl acetate
  3. customthe solvent removed under reduced pressure
  4. additionThe residue was diluted with water
  5. customthe solid that formed
  6. filtrationwas collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-f605f595b75b45398f611a91256eb0b7
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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