Dimethylformamide → HCID 21833680, compound

HRID 1740819Notes

Reaction equation

HRID 1740819 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 1334121-(4-Hydroxybenzyl)pyrazole

Product 1

HCID 21833680HCID 21833680, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 60 g of 4-(1-pyrazolyl)methylphenol, 54.9 g of ethyl chloroacetate, 95.1 g of potassium carbonate, and 500 ml of anhydrous dimethylformamide was heated at 50° C. under stirring for 5 hours, followed by cooling to room temperature. The reaction mixture was poured into 1 liter of water, which was extracted twice with 200 ml of ethyl acetate. The organic layers were combined, washed with water, saturated aqueous ammonium chloride solution and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to give crude ethyl 4-(l-pyrazolyl)methylphenoxyacetate as an oil.

Workup

  1. temperatureby cooling to room temperature
  2. extractionwas extracted twice with 200 ml of ethyl acetate
  3. washwashed with water, saturated aqueous ammonium chloride solution
  4. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2656e2d5e1447919a6d64abac51a39d
Source dataset
uspto-grants-1999_10
Patent number
US05972949

Reaction notes

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