Benzoyl chloride, 3-nitro- → (+/-)-cis-2-(4-methoxyphenyl)-3-(3-nitrobenzoyloxy)-5-[2-(dimethylamino)-ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1247981Notes

Reaction equation

HRID 1247981 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])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[N+:27]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34])([O-:29])=[O:28]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][CH:38]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=3)[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 91638Deacetyldiltiazem

Product 1

HCID 70518318(+/-)-cis-2-(4-methoxyphenyl)-3-(3-nitrobenzoyloxy)-5-[2-(dimethylamino)-ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.2 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in 10 ml of pyridine, and 0.66 g of 3-nitrobenzoyl chloride is added thereto. The mixture is stirred at room temperature for one hour. After the reaction, the mixture is poured into ice-water. The crystalline precipitates are collected by filtration and then recrystallized from a mixture of ethyl acetate and n-hexane. 1.26 g of (±)-cis-2-(4-methoxyphenyl)-3-(3-nitrobenzoyloxy)-5-[2-(dimethylamino)-ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as colorless prisms. Yield: 75%.

Workup

  1. customAfter the reaction
  2. customThe crystalline precipitates
  3. filtrationare collected by filtration
  4. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-7cc4acbed5ef4df68b3cea692657295a
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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