4-Fluorophenyl isocyanate → Cis-(+)-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-[(4-fluoro)-phenylcarbamoyloxy]-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H)-one

HRID 464245Notes

Reaction equation

HRID 464245 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][C@@H:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C@@H:7]([OH:24])[C:6]1=[O:25].[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>C1C=CC=CC=1>[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][C@@H:8]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C@@H:7]([O:24][C:35](=[O:36])[NH:34][C:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)[C:6]1=[O:25]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 91638Deacetyldiltiazem

Product 1

HCID 13579392Cis-(+)-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-[(4-fluoro)-phenylcarbamoyloxy]-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 Grams (0.268 mole) of the compound prepared under (A) were dissolved in 100 ml of anhydrous benzene and subsequently added with 3.02 ml (0.0269 mole) of 4-fluoro-phenylisocyanate, then the resulting solution was stirred on an oil bath at 30°-35° C. for 7 hours. After evaporating the solvent, the residue was taken up with anhydrous diethyl ether and the obtained white precipitate was recovered by filtration.

Workup

  1. customAfter evaporating the solvent
  2. filtrationthe obtained white precipitate was recovered by filtration

Sources & evidence

ORD record
ord-1169bdd26ac94eab95384bcaade7378f
Source dataset
uspto-grants-1985_10
Patent number
US04547495

Reaction notes

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