HCID 873944, compound → HCID 20516641, compound

HRID 1902372Notes

Reaction equation

HRID 1902372 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=O)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]>C1COCC1.Cl>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][NH:12][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 873944HCID 873944, compound

Product 1

HCID 20516641HCID 20516641, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Ethoxycarbonylphenyl)-(4-chlorophenyl)-acetamide (8.91 g., 0.03 mole) was dissolved in dry THF (70 ml) under nitrogen and borane-dimethyl sulphide complex (3.8 ml; 0.03 mole) was added at room temperature. The mixture was stirred for 30 minutes at room temperature, boiled under reflux with stirring for 4 hours, cooled and IN hydrochloric acid (70 ml) was added. The organic phase was separated, the aqueous layer extracted with dichloromethane (2×80 ml), the combined organic phases washed with water (100 ml) and dried over anhydrous magnesium sulphate. Evaporation of the solvent gave an oil which was chromatographed on silica-gel (120 g.) in dichloromethane to give ethyl 4-[2-(4-chlorophenyl)ethylamino]benzoate (4.02 g, 44%) melting at 75°-77° C.

Workup

  1. additionborane-dimethyl sulphide complex (3.8 ml; 0.03 mole) was added at room temperature
  2. temperatureunder reflux
  3. stirringwith stirring for 4 hours
  4. additionwas added
  5. customThe organic phase was separated
  6. extractionthe aqueous layer extracted with dichloromethane (2×80 ml)
  7. washthe combined organic phases washed with water (100 ml)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customEvaporation of the solvent
  10. customgave an oil which
  11. customwas chromatographed on silica-gel (120 g.) in dichloromethane

Sources & evidence

ORD record
ord-b85215cd3f624944abd97eabf07eeb5b
Source dataset
uspto-grants-1982_12
Patent number
US04362892

Reaction notes

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