Dimethylformamide → 4-[2-(Heptyloxy)ethoxy]-1-methyl-3,5-diphenyl-1H-pyrazole

HRID 1974362Notes

Reaction equation

HRID 1974362 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([O:15][CH2:16][CH2:17][OH:18])[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:5]1.CN(C=O)C.Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>O>[CH2:31]([O:18][CH2:17][CH2:16][O:15][C:7]1[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:5][N:4]([CH3:3])[C:8]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 123691-BromoheptaneHCID 24758Sodium hydrideHCID 213980492-[(1-Methyl-3,5-diphenyl-1H-pyrazol-4-yl)oxy]ethan-1-ol

Product 1

HCID 213981284-[2-(Heptyloxy)ethoxy]-1-methyl-3,5-diphenyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (0.89 g, 57%, 0.02 mole) is added to a solution of 2-[(1-methyl-3,5-diphenyl-4-pyrazolyl)oxy]-ethanol (5.9 g, 0.02 mole) and dry DMF (50 ml). The reaction mixture is stirred and heated to 80°-90° C. The stirred mixture is allowed to cool. This mixture is added to a solution of 1-bromoheptane (9 g, 0.05 mole) and dry DMF (75 ml). After heating at 80°-90° C for 4 hours, the stirred reaction mixture is poured into water.

Workup

  1. temperatureheated to 80°-90° C
  2. temperatureto cool
  3. temperatureAfter heating at 80°-90° C for 4 hours
  4. customthe stirred reaction mixture

Sources & evidence

ORD record
ord-96862430080442d4b29115ad8e3724a0
Source dataset
uspto-grants-1976_12
Patent number
US04000301

Reaction notes

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