Acetic Acid → 2,5-Dihydro-4-methyl-2-(2,3-dichlorophenyl)-1,5-benzothiazepine-3-carboxylic acid, methyl ester

HRID 1906720Notes

Reaction equation

HRID 1906720 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([C:15](=O)[CH3:16])[C:11]([O:13][CH3:14])=[O:12].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].C(O)(=O)C>CN(C)C=O.CCOCC>[CH3:16][C:15]1[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:25][CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 87132-AminothiophenolHCID 54242386Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester

Product 1

HCID 138264012,5-Dihydro-4-methyl-2-(2,3-dichlorophenyl)-1,5-benzothiazepine-3-carboxylic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(2,3-dichlorophenyl)methylene]-3-oxobutanoic acid, methyl ester (1.0 g., 3.66 mmole) in dry dimethylformamide (7 ml.) is treated with 2-aminothiophenol (512 mg., 4.1 mmoles) and the resulting reaction mixcture is stirred at room temperature for 3 hours. Acetic acid (0.1 ml.) is added and the reaction is heated at 75° (oil bath temperature) for 48 hours. It is then cooled to room temperature and diluted with ether. The resulting solution is washed with 1N sodium hydroxide, water, and brine. After drying over anhydrous magnesium sulfate, the solvent is stripped off to provide a yellow solid. It is crystallized from isopropyl ether-dichloromethane to yield 660 mg. of light yellow crystalline product. Recrystallization from isopropyl ether-dichloromethane yields an analytically pure sample of 2,5-dihydro-4-methyl-2-(2,3-dichlorophenyl)-1,5-benzothiazepine-3-carboxylic acid, methyl ester as colorless needles; m.p. 190°-191°. TLC (silica gel; ethyl acetate:hexanes, 40:60) Rf =0.40.

Workup

  1. customthe resulting reaction mixcture
  2. temperaturethe reaction is heated at 75° (oil bath temperature) for 48 hours
  3. temperatureIt is then cooled to room temperature
  4. washThe resulting solution is washed with 1N sodium hydroxide, water, and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customto provide a yellow solid
  7. customIt is crystallized from isopropyl ether-dichloromethane
  8. customto yield 660 mg
  9. customRecrystallization from isopropyl ether-dichloromethane

Sources & evidence

ORD record
ord-67f7cde98c264f379f2d3e8e98c64ca5
Source dataset
uspto-grants-1987_03
Patent number
US04654335

Reaction notes

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