Dimethylformamide → HCID 53736602, compound

HRID 1740823Notes

Reaction equation

HRID 1740823 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[CH:5]=[CH:4][C:3]=1[OH:14].Cl[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[CH:5]=[CH:4][C:3]=1[O:14][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 21833668HCID 21833668, compound

Product 1

HCID 53736602HCID 53736602, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.0 g of 2-chloro-4-(1-pyrazolyl)methylphenol (produced in Reference Production Example 2), 7.6 g of ethyl chloroacetate, 13.2 g of potassium carbonate and 100 ml of anhydrous dimethylformamide was heated at 50° C. under stirring for 5 hours, and then cooled to room temperature. The reaction mixture was poured into 500 ml of water, which was extracted twice with 50 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 2-chloro-4-(1-pyrazolyl)methylphenoxyacetate as an oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionwas extracted twice with 50 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-53dc94e8e5da4ce2b3ca9526481c709e
Source dataset
uspto-grants-1999_10
Patent number
US05972949

Reaction notes

Loading…