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

HRID 1162158Notes

Reaction equation

HRID 1162158 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) were charged to a flask fitted with a reflux condenser. A solution of NaOH (3 eq., 50% aq.) was added and the mixture heated to 70° C. for 30-40 minutes. EtOAc was removed by distillation at 100 mm Hg and the mixture was cooled to 5° C. The mixture was acidified with 6N HCl to pH 2. The solid was then collected by vacuum filtration and washed with water (390 mL). The solid was taken up in CH2Cl2 (520 mL) and washed with saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated to give the desired material (174 g, 87%).

Workup

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

Sources & evidence

ORD record
ord-a3b16339c90c4cb3972ef0d67d723db3
Source dataset
uspto-grants-2010_10
Patent number
US07820685B2

Reaction notes

Loading…