Potassium Carbonate → (+)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1247997Notes

Reaction equation

HRID 1247997 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=3[Cl:27])[C:14](=[O:29])[NH:13][C:12]3[CH:30]=[CH:31][CH:32]=[CH:33][C:11]=3[S:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44]Cl>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=3[Cl:27])[C:14](=[O:29])[N:13]([CH2:44][CH2:43][N:42]([CH3:46])[CH3:41])[C:12]3[CH:30]=[CH:31][CH:32]=[CH:33][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 70381329(-)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 70380953(+)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

970 mg of (-)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in 15 ml of acetone, and 690 mg of potassium carbonate and 375 mg of 2-(dimethylamino)ethyl chloride hydrochloride are added thereto. The mixture is refluxed for 6 hours under stirring. After the reaction, the mixture is evaporated under reduced pressure to remove solvent. Ethyl acetate is added to the residue, and the mixture is washed with water. The ethyl acetate solution is dried and evaporated under reduced pressure to remove solvent. The residue is dissolved in ethanol under heating, and the mixture is allowed to stand. Crystalline precipitates are collected by filtration and dried, whereby 810 mg of (+)-cis-2-(4-methoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as pale yellow needles. Yield: 73%.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customAfter the reaction
  3. customthe mixture is evaporated under reduced pressure
  4. customto remove solvent
  5. additionEthyl acetate is added to the residue
  6. washthe mixture is washed with water
  7. dry with materialThe ethyl acetate solution is dried
  8. customevaporated under reduced pressure
  9. customto remove solvent
  10. dissolutionThe residue is dissolved in ethanol
  11. temperatureunder heating
  12. customCrystalline precipitates
  13. filtrationare collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-fdb7ce66a9934682bc14803d03581c1e
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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