1-Bromo-3-chloropropane → HCID 15223430, compound

HRID 1768536Notes

Reaction equation

HRID 1768536 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.Br[CH2:24][CH2:25][CH2:26][Cl:27].C([O-])([O-])=O.[K+].[K+]>CC(C)=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]([CH2:24][CH2:25][CH2:26][Cl:27])[C:12]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 155934012-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 15223430HCID 15223430, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8.395 g (25.0 mmol) of 2-(4-methoxyphenyl)-3-hydroxy-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (IV-1), 4.723 g (30.0 mmol) of 1-bromo-3-chloropropane (V-1) and 4.146 g (30.0 mmol) of K2CO3 were dissolved in 168 ml of acetone, and the mixture was refluxed for 20 hours. The reaction mixture was evaporated under reduced pressure to give a residue, which was chromatographed on silica gel to give 10.96 g of cis-2-(4-methoxyphenyl)-3-hydroxy-5-(3-chloropropyl)-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (III-1) from dichloromethane effluent parts. The obtained compound was recrystallized from ethyl acetate to give 9.146 g as colorless prisms in 88.7% yield.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customto give a residue, which
  4. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-828be809aaab40a18c97d4f28042ddfa
Source dataset
uspto-grants-1995_01
Patent number
US05378698

Reaction notes

Loading…