Hydrochloric Acid → HCID 14391423, compound

HRID 1638238Notes

Reaction equation

HRID 1638238 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])=[O:7])=[CH:4][CH:3]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Cl:16][C:10]1[C:11]([Cl:15])=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:18][CH:17]=1)=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 12770927HCID 12770927, compound

Product 1

HCID 14391423HCID 14391423, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28.2 g of 4-hydroxy-N-(2,3-dichlorophenyl)-benzamide, 20.0 g of ethyl bromoacetate and 20.7 g of potassium carbonate were dispersed in 150 ml of N,N-dimethylformamide, and the dispersion was stirred at a temperature of from 120° to 140° C. for 4 hours. After completion of the reaction, the reaction solution was poured into 500 ml of a 2% hydrochloric acid aqueous solution. The crude product obtained by collecting precipitates by filtration, was recrystallized from toluene to obtain 34.5 g of desired ethyl 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetate. Yield: 93.4% Melting point: 126°-129° C.

Workup

  1. customAfter completion of the reaction
  2. customThe crude product obtained
  3. customby collecting
  4. customprecipitates by filtration
  5. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-fe175aa259574859a10669f0c25781a6
Source dataset
uspto-grants-1989_11
Patent number
US04878942

Reaction notes

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