5-Chloro-2-methoxybenzoyl chloride → 2-Ethoxy-4-(5-chloro-2-methoxy-benzamido)-benzoic acid ethyl ester

HRID 27467Notes

Reaction equation

HRID 27467 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[O:12][CH2:13][CH3:14])[CH3:2].[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21]([CH:25]=1)[C:22](Cl)=[O:23]>C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:22](=[O:23])[C:21]2[CH:25]=[C:17]([Cl:16])[CH:18]=[CH:19][C:20]=2[O:26][CH3:27])=[CH:7][C:6]=1[O:12][CH2:13][CH3:14])[CH3:2]

Participants

5

Reactant 2

HCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 54179514Benzoic acid, 4-amino-2-ethoxy-, ethyl ester

Product 1

HCID 538402982-Ethoxy-4-(5-chloro-2-methoxy-benzamido)-benzoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

10.4 g of 2-ethoxy-4-amino-benzoic acid ethyl ester were suspended in a mixture of 6.8 ml of triethylamine and 200 ml of toluene and 10.3 g of 5-chloro-2-methoxy-benzoyl chloride dissolved in a small amount of toluene were added dropwise. The whole was stirred for 3 hours under reflux and, after cooling, it was washed with water, dilute hydrochloric acid and a sodium bicarbonate solution and dried over sodium sulfate. Upon concentration of the solution under reduced pressure, the 2-ethoxy-4-(5-chloro-2-methoxy-benzamido)-benzoic acid ethyl ester was obtained in the form of a solid product having a crude melting point of 108°-111° C.

Workup

  1. additionwere added dropwise
  2. temperatureunder reflux
  3. temperatureafter cooling
  4. washit was washed with water, dilute hydrochloric acid
  5. dry with materiala sodium bicarbonate solution and dried over sodium sulfate

Sources & evidence

ORD record
ord-72bd60edce5b4c00965ff9f142800b3b
Source dataset
uspto-grants-1980_09
Patent number
US04221815

Reaction notes

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