Dimethylformamide → HCID 19982274, compound

HRID 1460715Notes

Reaction equation

HRID 1460715 reaction equation
[H-].[Na+].CN(C=O)C.[C:8]1([C:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][NH:16][N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34]>O.C(OCC)C>[C:8]1([C:14]2[C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:17][N:16]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 3017433,4-DiphenylpyrazoleHCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 19982274HCID 19982274, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride (1.57 g of 50% dispersion, 32 mmol) was washed twice with hexanes, covered with DMF (100 mL), and a mixture of 3,4-diphenyl-1H-pyrazole and 4,5-diphenyl-1H-pyrazole (6.00 g, 27 mmol) was added. After gas evolution had ceased, the mixture was stirred for 10 minutes before adding methyl 8-bromooctanoate (7.10 g, 30 mmol). The mixture was stirred at room temperature for 40 minutes, diluted with water, and extracted with diethyl ether (3 times). The combined extracts were washed with water (3 times), dried over sodium sulfate, and concentrated in vacuo to leave an oil. Repeated chromatography on a column of silica gel using a mixture of hexanes and diethyl ether (2:1) as eluant provided methyl 3,4-diphenyl-1H-pyrazole-1-octanoate (6.11 g, 59%) as an oil. MS(CI): m/e=377 (MH+).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 40 minutes
  3. extractionextracted with diethyl ether (3 times)
  4. washThe combined extracts were washed with water (3 times)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto leave an oil

Sources & evidence

ORD record
ord-a2c7170e6abf4ebdb0e6d67e500d150a
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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