Formaldehyde → Ro 14-7437

HRID 2198723Notes

Reaction equation

HRID 2198723 reaction equation
[NH2:1][C:2](=[C:8]1[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=2[NH:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:21]=O>C(Cl)Cl>[CH3:15][N:13]1[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=2[N:9]2[CH:21]=[N:1][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]2[CH2:14]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 70541641ethyl alpha-amino-1,3,4,5-tetrahydro-4-methyl-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate

Product 1

HCID 127597Ro 14-7437

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 g of ethyl α-amino-1,3,4,5-tetrahydro-4-methyl-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate are dissolved in 20 ml of methylene chloride, treated with 0.65 ml of 37 percent aqueous formaldehyde solution and stirred in the presence of air at room temperature for 2 hours. The solution is subsequently washed twice with 10 ml of water each time. The organic phase is separated, dried and decolourised with active carbon. After filtration of the carbon, the filtrate is evaporated in vacuo and the residue is chromatographed on 20 g of silica gel. Elution is carried out firstly with chloroform and subsequently with chloroform/ethanol (985:15). The fractions which contain ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate as the main component are combined and evaporated in vacuo. The residue is dissolved in ethanol and crystallised by the addition of diisopropyl ether. There is obtained ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 162°-164° C.

Workup

  1. washThe solution is subsequently washed twice with 10 ml of water each time
  2. customThe organic phase is separated
  3. customdried
  4. filtrationAfter filtration of the carbon
  5. customthe filtrate is evaporated in vacuo
  6. customthe residue is chromatographed on 20 g of silica gel
  7. washElution
  8. customevaporated in vacuo
  9. dissolutionThe residue is dissolved in ethanol
  10. customcrystallised by the addition of diisopropyl ether

Sources & evidence

ORD record
ord-2e375b80dbe64c7c83c23c173f5f6a79
Source dataset
uspto-grants-1982_11
Patent number
US04359420

Reaction notes

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