Acetone → HCID 70484071, compound

HRID 280522Notes

Reaction equation

HRID 280522 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[C:19]([Cl:23])[C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28]Cl.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:28][CH2:27][N:26]([CH3:30])[CH3:25])[C:12]3[CH:18]=[C:19]([Cl:23])[C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 70483039HCID 70483039, compound

Product 1

HCID 70484071HCID 70484071, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.48 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-7,8-dichloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 0.64 g of 2-(dimethylamino)ethyl chloride hydrochloride, 1.66 g of potassium carbonate, 45 ml of acetone and 0.5 ml of water is refluxed for 22 hours. After the reaction is completed, insoluble materials are removed by filtration. The filtrate is evaporated to remove solvent, and diisopropyl ether is added to the residue. The precipitated crystals are collected by filtration and then recrystallized from ethyl acetate. 1.18 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-7,8-dichloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained.

Workup

  1. temperatureis refluxed for 22 hours
  2. custominsoluble materials are removed by filtration
  3. customThe filtrate is evaporated
  4. customto remove solvent, and diisopropyl ether
  5. additionis added to the residue
  6. filtrationThe precipitated crystals are collected by filtration
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c96557854cb346dcae8a26bc5db1fb32
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

Loading…