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1,2-Dichloroethane → 6-phenyl-8-chloro-4H-s-triazolo [4,3-a][1,4]benzodiazepine-1-carbonitrile

HRID 1605031
Notes
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Reaction equation

HRID 1605031 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([C:12]2[C:18]3[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=3[N:16]3[C:24]([C:27]([NH2:29])=O)=[N:25][N:26]=[C:15]3[CH2:14][N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(Cl)CCl>CN(C)C=O>[C:6]1([C:12]2[C:18]3[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=3[N:16]3[C:24]([C:27]#[N:29])=[N:25][N:26]=[C:15]3[CH2:14][N:13]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24813Phosphorus oxychlorideHCID 214860186-phenyl-8-chloro-4H-s-triazolo [4,3-a][1,4]benzodiazepine-1-carboxamide

Product 1

HCID 125624996-phenyl-8-chloro-4H-s-triazolo [4,3-a][1,4]benzodiazepine-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 ml of phosphorous oxychloride is added to a solution of 1.69 g (0.005 mole) of 6-phenyl-8-chloro-4H-s-triazolo[4,3-a] [1,4]benzodiazepine-1-carboxamide in 5 ml of dimethylformamide, and stirring maintained for 10 minutes at 80°. The reaction mixture is then poured on ice and extraced with ethylene chloride. The extract is washed with water and saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. The residue is chromatographed on silica gel with the use of benzene and benzene/ethyl acetate mixtures as eluant. The fractions containing the desired nitrile [Rf = 0.5 in the eluant system benzene/chloroform/ethyl acetate (4:4:2)] are combined and concentrated by evaporation. The residue is crystallised from ethyl acetate/petroleum ether to obtain 6-phenyl-8-chloro-4H-s-triazolo [4,3-a][1,4]benzodiazepine-1-carbonitrile, M.P. 191°-192°.

Workup

  1. temperaturemaintained for 10 minutes at 80°
  2. additionThe reaction mixture is then poured on ice
  3. washThe extract is washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel with the use of benzene and benzene/ethyl acetate
  7. additionThe fractions containing the desired nitrile [Rf = 0.5 in the eluant system benzene/chloroform/ethyl acetate (4:4:2)]
  8. concentrationconcentrated by evaporation
  9. customThe residue is crystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-b15c3bc5530d4a6785fd7433d3de26d2
Source dataset
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03948931

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes