Water → HCID 20542076, compound

HRID 2286162Notes

Reaction equation

HRID 2286162 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16](I)[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:20])[CH:10]([CH3:21])[N:9]=1.[Cu][C:23]#[N:24].O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:23]#[N:24])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:20])[CH:10]([CH3:21])[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 148519365-(o-fluorophenyl)-1,3-dihydro-7-iodo-3-methyl-2H-1,4-benzodiazepin-2-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 20542076HCID 20542076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

23.2 g (58.8 mmol) of 5-(o-fluorophenyl)-1,3-dihydro-7-iodo-3-methyl-2H-1,4-benzodiazepin-2-one and 10 g (0.11 mol) of copper (I) cyanide in 250 ml of dimethylformamide are heated at 150° for 2 hours under argon. After cooling, 700 ml of water are added to the mixture and the resulting precipitate is filtered off. This is dissolved in 1 l of water/ethylenediamine (1:1) and extracted with 1 l of methylene chloride; the separated aqueous phase is extracted a further twice with methylene chloride. The combined organic extracts are washed with water, dried and evaporated. The residue gives, from cyclohexane, 5-(o-fluorophenyl)-2,3-dihydro-3-methyl-2-oxo-1H-1,4-benzodiazepine-7-carbonitrile of melting point 216°.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate is filtered off
  3. dissolutionThis is dissolved in 1 l of water/ethylenediamine (1:1)
  4. extractionextracted with 1 l of methylene chloride
  5. extractionthe separated aqueous phase is extracted a further twice with methylene chloride
  6. washThe combined organic extracts are washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-2e052f31246c41289dbd9c8324c0424b
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

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