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

HRID 1247982Notes

Reaction equation

HRID 1247982 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:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33])([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:32](=[O:33])[C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[N+:27]([O-:29])=[O:28])[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 118752-Nitrobenzoyl chlorideHCID 91638Deacetyldiltiazem

Product 1

HCID 70517050(+/-)-cis-2-(4-methoxyphenyl)-3-(2-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 84%

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 2-nitrobenzoyl chloride is added thereto. The mixture is stirred at room temperature for 2 hours. 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. 1.41 g of (±)-cis-2-(4-methoxyphenyl)-3-(2-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are thereby obtained as colorless needles. Yield: 84%.

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-c79c297ab2f74bff9196ebda96d5ed71
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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