Hydrochloric Acid → Benzamide

HRID 236869Notes

Reaction equation

HRID 236869 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5](OC)=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl.C(C1C=CC(CC[NH2:24])=CC=1)C.N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[C:7]([NH2:24])(=[O:8])[C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 213155294-Ethylbenzeneethanamine hydrochloride

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 4.1 g of 5-chloro-2-methoxy-benzoyl chloride in 20 ml of toluene was added dropwise to a suspension of 4.65 g of 2-(4-ethylphenyl)-ethylamine hydrochloride in 100 ml of anhydrous toluene after addition of 5 ml of pyridine. The whole was heated under reflux, then shaken with water, dilute hydrochloric acid and a solution of sodium bicarbonate and dried over sodium sulfate. After concentration under reduced pressure, the residue, which solidified only slowly, was filtered off with suction after addition of petroleum ether (B.p. 30°-60° C.). The 5-chloro-2-methoxy-N-(2-<4-ethylphenyl>-ethyl)-benzamide so obtained was found to melt at 66°-68° C.

Workup

  1. temperatureThe whole was heated
  2. temperatureunder reflux
  3. dry with materiala solution of sodium bicarbonate and dried over sodium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. filtrationwas filtered off with suction
  6. additionafter addition of petroleum ether (B.p. 30°-60° C.)

Sources & evidence

ORD record
ord-8873582cdcbd4096a46fbee0bab7ceb6
Source dataset
uspto-grants-1979_06
Patent number
US04158063

Reaction notes

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