Ethyl Acetate → 2-chloro-N-(4-mercaptophenyl)benzamide

HRID 499102Notes

Reaction equation

HRID 499102 reaction equation
ClC1C=CC=CC=1C(=O)[S:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[CH:8][CH:7]=1.CCOC(C)=O.[OH-].[Na+]>O>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([SH:5])=[CH:7][CH:8]=1)=[O:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59520030S-4-(2-chlorobenzamido)phenyl 2-chlorobenzothioate

Product 1

HCID 271374192-chloro-N-(4-mercaptophenyl)benzamideYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

S-4-(2-chlorobenzamido)phenyl 2-chlorobenzothioate (305 g, 0.76 mol), EtOAc (325 mL), and water (65 mL) are charged to a flask fitted with reflux condenser. A solution of NaOH (3 eq., 50% aq.) is added and the mixture heated to 70° C. for 30-40 minutes. EtOAc was removed by distillation at 100 mm Hg and the mixture cooled to 5° C. The mixture was acidified with 6N HCl to pH 2. The solid is collected by vacuum filtration and washed with water (390 mL). The solid is taken up in CH2Cl2 (520 mL) and washed with saturated aqueous NaHCO3. The organic layer is dried over Na2SO4, filtered, and concentrated to give the desired material (174 g, 87%).

Workup

  1. customfitted
  2. temperaturewith reflux condenser
  3. customEtOAc was removed by distillation at 100 mm Hg
  4. temperaturethe mixture cooled to 5° C
  5. filtrationThe solid is collected by vacuum filtration
  6. washwashed with water (390 mL)
  7. washwashed with saturated aqueous NaHCO3
  8. dry with materialThe organic layer is dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-68ddf14e51274af0a803e598fae059ea
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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