Acetone → HCID 67941806, compound

HRID 978339Notes

Reaction equation

HRID 978339 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]=[CH:19][CH:20]=[C:21]([Cl:22])[C:11]=3[S:10]2)=[CH:5][CH:4]=1.Cl.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[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])[N:13]([CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])[C:12]3[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 13604062HCID 13604062, compound

Product 1

HCID 67941806HCID 67941806, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.01 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-9-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 0.95 g of 2-(dimethylamino)ethyl chloride hydrochloride, 2.49 g of powdered potassium carbonate, 60 ml of acetone and 0.6 ml of water is refluxed for 23 hours. After the reaction is completed, insoluble materials are removed by filtration. The filtrate is evaporated to remove solvent. The residue is digested with isopropyl ether and the resultant crystals are collected by filtration and recrystallized from ethyl acetate. 1.84 g of (±)-cis-2-(4-methoxypheny)-3-hydroxy-5-[2-(dimethylamino)ethyl]-9-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained. Yield: 75.4%

Workup

  1. temperatureis refluxed for 23 hours
  2. custominsoluble materials are removed by filtration
  3. customThe filtrate is evaporated
  4. customto remove solvent
  5. filtrationthe resultant crystals are collected by filtration
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-699b87cc9d7c417c9a6f7f1c37fcae6d
Source dataset
uspto-grants-1987_05
Patent number
US04665068

Reaction notes

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