Sodium Carbonate → (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-(4-nitrobenzyl)-1H-1,4-benzodiazepine dihydrochloride

HRID 48348Notes

Reaction equation

HRID 48348 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH:7]=[CH:8][C:9]1=[N:10][CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2.[N+:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1)([O-:26])=[O:25].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(OCC)(=O)C.O>[ClH:3].[ClH:1].[Cl:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH:7]=[CH:8][C:9]1=[N:10][CH2:11][CH2:12][N:13]([CH2:31][C:30]2[CH:33]=[CH:34][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 660114-Nitrobenzyl bromideHCID 69893336(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-benzo-1,4-diazepine dihydrochloride

Product 1

HCID 69893093(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-(4-nitrobenzyl)-1H-1,4-benzodiazepine dihydrochlorideYield 15.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 117 mg (0.3 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-benzo-1,4-diazepine dihydrochloride, 70 mg (0.32 mmol) of 4-nitrobenzyl bromide and 127 mg (1.2 mmol) of sodium carbonate were heated at 70° C. in 3 ml of ethanol for 18 hours. The mixture was diluted with ethyl acetate and water and the organic phase dried over magnesium sulphate, filtered and evaporated to dryness. The residue was chromatographed three times on silica gel using ethyl acetate/petrol (3:1), dichloromethane/methanol (97:3) and ethyl acetate/petrol (9:1) for the elutions. The product was dissolved in a solution of hydrogen chloride in methanol, evaporated to dryness and the residue triturated with diethyl ether to give 12 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-(4-nitrobenzyl)-1H-1,4-benzodiazepine dihydrochloride. MS: m/e 451.9 [M+H]+.

Workup

  1. dry with materialthe organic phase dried over magnesium sulphate
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe residue was chromatographed three times on silica gel
  5. dissolutionThe product was dissolved in a solution of hydrogen chloride in methanol
  6. customevaporated to dryness
  7. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-06e8eb8492714e5eb36b5255c8565a30
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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