3,4-Dinitrobenzoic acid → HCID 86740136, compound

HRID 1247984Notes

Reaction equation

HRID 1247984 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][C:38]=1[N+:39]([O-:41])=[O:40])[C:33](O)=[O:34])([O-:29])=[O:28].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[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][C:38]([N+:39]([O-:41])=[O:40])=[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

5

Reactant 3

HCID 107093,4-Dinitrobenzoic acidHCID 10868DicyclohexylcarbodiimideHCID 91638Deacetyldiltiazem

Product 1

HCID 86740136HCID 86740136, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.2 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 1.16 g of 3,4-dinitrobenzoic acid and 0.76 g of dicyclohexylcarbodiimide are dissolved in 20 ml of methylene chloride, and the solution is stirred at room temperature overnight. After the reaction, the precipitates are collected by filtration. The filtrate is washed with water, dried and then evaporated to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:methanol=100:3), whereby 0.8 g of (+)-cis-2-(4-methoxyphenyl)-3-(3,4-dinitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is obtained as an oil.

Workup

  1. customAfter the reaction
  2. filtrationthe precipitates are collected by filtration
  3. washThe filtrate is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel chromatography (solvent, chloroform:methanol=100:3)

Sources & evidence

ORD record
ord-ff775064af18435483cd506eb87e1229
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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