Dimethylformamide → 6-cyano-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione

HRID 223190Notes

Reaction equation

HRID 223190 reaction equation
I[C:2]1[C:7]2[C:8](=[O:15])[N:9]([CH3:14])[CH2:10][C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cu][C:17]#[N:18].CN(C)C=O>O>[CH3:14][N:9]1[C:8](=[O:15])[C:7]2=[C:2]([C:17]#[N:18])[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])[CH2:10]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 20487136HCID 20487136, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 201389616-cyano-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.7 g (0.018 mol) of 3,4-dihydro-6-iodo-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione, 2.4 g (0.026 mol) of copper (I) cyanide and 60 ml of dimethylformamide is heated to 50° for 45 minutes. After cooling, the mixture is diluted with water and extracted several times with chloroform/isopropanol (4:1). The combined organic extracts are dried over magnesium sulphate and evaporated. The yellow-brown crude product is recrystallized from methanol, there being obtained 2,3,4,5-tetrahydro-4-methyl-2,5-dioxo-1H-1,4-benzodiazepine-6-carbonitrile of melting point 253-256.

Workup

  1. temperatureis heated to 50° for 45 minutes
  2. temperatureAfter cooling
  3. extractionextracted several times with chloroform/isopropanol (4:1)
  4. dry with materialThe combined organic extracts are dried over magnesium sulphate
  5. customevaporated
  6. customThe yellow-brown crude product is recrystallized from methanol, there

Sources & evidence

ORD record
ord-382cf3c6241a41ffaa1e1fff1dc0a679
Source dataset
uspto-grants-1982_10
Patent number
US04352817

Reaction notes

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