Sodium Dithionite → 2-Amino-4-methyl-3-phenyl-3,4-dihydro-5H-1,4-benzodiazepin-5-one

HRID 437339Notes

Reaction equation

HRID 437339 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].O[N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14](=[O:21])[N:13]([CH3:22])[CH:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]1=[NH:29]>O.C(O)C>[NH2:29][C:11]1[CH:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:13]([CH3:22])[C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:10]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 21428199HCID 21428199, compound

Product 1

HCID 214282132-Amino-4-methyl-3-phenyl-3,4-dihydro-5H-1,4-benzodiazepin-5-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A slow stream of a solution of 23.00 g (0.132 m) of sodium dithionite in 300 ml of water is added to a stirred solution of 16.87 g (0.06 m) of 1-hydroxy-2-imino-4-methyl-3-phenyl-1,2,3,4-tetrahydro-5H-1,4-benzodiazepine-5-one in 700 ml of ethanol. The reaction mixture is refluxed for 2 hours and then concentrated in vacuo, to about 200 ml. The resulting solution is extracted once with chloroform. Some solid crude product, formed during this extraction, is filtered off. The aqueous layer is made basic and extracted with chloroform. The organic solutions are combined, dried and concentrated to dryness in vacuo to give additional solid product. The solids are combined and recrystallized twice from ethanol/ether (the solution is filtered while hot to clarify) to give the pure product, 2-amino-3,4-dihydro-4-methyl-3-phenyl-5H-1,4-benzodiazepine-5-one m.p. 282° - 286° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. concentrationconcentrated in vacuo, to about 200 ml
  3. extractionThe resulting solution is extracted once with chloroform
  4. customSome solid crude product, formed during this extraction
  5. filtrationis filtered off
  6. extractionextracted with chloroform
  7. customdried
  8. concentrationconcentrated to dryness in vacuo
  9. customto give additional solid product
  10. customrecrystallized twice from ethanol/ether (the solution
  11. filtrationis filtered while hot

Sources & evidence

ORD record
ord-f9efcf76ae69464697eb6e3e8804e5f5
Source dataset
uspto-grants-1977_06
Patent number
US04031079

Reaction notes

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