O-Xylene → HCID 15593400, compound

HRID 653805Notes

Reaction equation

HRID 653805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[SH:9].C[O:11][C:12](=O)[C:13]1(C2C=CC(OC)=CC=2)[O:15]C1.[OH2:25].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29](S(O)(=O)=O)=[CH:28][CH:27]=1.[C:37]1(C)C(C)=CC=CC=1>C1(C)C=CC=CC=1>[CH3:37][O:25][C:29]1[CH:30]=[CH:31][C:26]([C@H:36]2[C@@H:13]([OH:15])[C:12](=[O:11])[NH:1][C:2]3[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=3[S:9]2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 521998p-Toluenesulfonic acid monohydrateHCID 27375182-Amino-5-chlorobenzenethiolHCID 23036167HCID 23036167, compound

Product 1

HCID 15593400HCID 15593400, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 400 ml of toluene are dissolved 24.0 g of 2-amino-5-chlorothiophenol and 31.2 g of (4-methoxyphenyl)glycidic acid methyl ester, and the solution is refluxed under nitrogen atmosphere for 2 hours. To the reaction mixture are added 1.43 g of p-toluenesulfonic acid hydrate and 350 ml of xylene and the mixture is refluxed for 2 hours and simultaneously 350 ml of the solvent is distilled. After cooling, precipitated crystals are collected by filtration to give 19.8 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one.

Workup

  1. temperaturethe solution is refluxed under nitrogen atmosphere for 2 hours
  2. temperaturethe mixture is refluxed for 2 hours
  3. distillationsimultaneously 350 ml of the solvent is distilled
  4. temperatureAfter cooling
  5. customprecipitated crystals
  6. filtrationare collected by filtration

Sources & evidence

ORD record
ord-761b635eb15e4427b41527be6cc8e4d0
Source dataset
uspto-grants-1992_07
Patent number
US05128469

Reaction notes

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