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

HRID 1995510Notes

Reaction equation

HRID 1995510 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>[C:17]([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)#[N:18]

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 6-cyano-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione of melting point 253°-256° (decomposition).

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-b17452bb258a4d8e910acb0ac7d3a224
Source dataset
uspto-grants-1983_09
Patent number
US04405516

Reaction notes

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