Hydrochloric Acid → HCID 23453113, compound

HRID 1277658Notes

Reaction equation

HRID 1277658 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:25])=[C:19]([CH:23]=1)[C:20](Cl)=[O:21].Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O.N1C=CC=CC=1>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:25])=[C:19]([CH:23]=1)[C:20]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)=[O:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 225219p-Aminophenylacetic acid ethyl esterHCID 516892Sodium BicarbonateHCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 23453113HCID 23453113, compoundYield 70.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent3×

Procedure

8.9 g Ethyl 4-aminophenylacetate are suspended in 200 ml. toluene. After the addition of 4 ml pyridine, a solution of 10.2 g 5-chloro-2-methoxybenzoyl chloride in 10 ml toluene is added dropwise thereto and the reaction mixture heated under reflux for 2 hours. After cooling, the toluene phase is successively shaken out with dilute hydrochloric acid, aqueous sodium bicarbonate solution and water and thereafter dried and evaporated. The evaporation residue is then recrystallized twice from ethanol to give 12.2 g (70% of theory) ethyl 4-(5-chloro-2-methoxybenzamido)-phenylacetate; m.p. 104° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customdried
  5. customevaporated
  6. customThe evaporation residue is then recrystallized twice from ethanol

Sources & evidence

ORD record
ord-d26a15e9dc764f29bb76079878eee4a7
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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