Dimethyl Sulfoxide → 3-acetoxy-8-chloro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

HRID 1033482Notes

Reaction equation

HRID 1033482 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7](=[O:20])[CH:8]([OH:19])[CH:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:10][C:4]=2[CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].CS(C)=O.N1C=CC=CC=1>O.C1(C)C=CC=CC=1>[C:23]([O:19][C:8]1[C:7](=[O:20])[NH:6][C:5]2[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][C:4]=2[S:10][C:9]=1[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 155934012-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 190261363-acetoxy-8-chloro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-oneYield 60.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 8-chloro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (36.0 g), acetic anhydride (50 ml), dimethylsulfoxide (100 ml), pyridine (3 ml) and toluene (100 ml) is stirred at room temperature for 3 days. Water is added to the mixture, and the mixture is extracted with ethyl acetate, and the extract is washed with water, and dried. The resultant is evaporated to remove the solvent, and diethyl ether is added to the residue. The precipitated crystal is collected by filtration to give 3-acetoxy-8-chloro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (24.5 g).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe extract is washed with water
  3. customdried
  4. customThe resultant is evaporated
  5. customto remove the solvent, and diethyl ether
  6. additionis added to the residue
  7. filtrationThe precipitated crystal is collected by filtration

Sources & evidence

ORD record
ord-fbc01b5d33b64c8f8b8e8c8beb1e7f95
Source dataset
uspto-grants-1994_05
Patent number
US05310904

Reaction notes

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