7-(Hydroxyamino)-1-(methoxymethyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one → HCID 12317900, compound

HRID 1729603Notes

Reaction equation

HRID 1729603 reaction equation
[OH:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][O:14][CH3:15])[C:11](=[O:16])[CH2:10][N:9]=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]=2[CH:23]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH3:15][O:14][CH2:13][N:12]1[C:6]2[CH:5]=[CH:4][C:3]([N:2]=[O:1])=[CH:23][C:7]=2[C:8]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:9][CH2:10][C:11]1=[O:16]

Participants

4

Reactant 1

HCID 3248157-(Hydroxyamino)-1-(methoxymethyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 12317900HCID 12317900, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

30 g. of Manganese dioxide was added to a solution of 3.1 g. (0.01 mole) of 1,3-dihydro-7-hydroxyamino-1-methoxymethyl-5-phenyl-2H-1,4-benzodiazepin-2-one in 200 ml. of methylene chloride. After stirring for 10 minutes at room temperature the inorganic material was filtered off and the filtrate was evaporated to leave an oil with a greenish tint. Since crystallization attempts were unsuccessful the material was purified by chromatography over 50 g. of silica gel using 5% ethylacetate in methylene chloride. The thin layer chromatographically pure fractions still did not crystallize.

Workup

  1. filtrationwas filtered off
  2. customthe filtrate was evaporated
  3. customto leave an oil with a greenish tint
  4. customSince crystallization attempts
  5. customwas purified by chromatography over 50 g
  6. customThe thin layer chromatographically pure fractions still did not crystallize

Sources & evidence

ORD record
ord-693720ce02a04273918655059549816d
Source dataset
uspto-grants-1976_11
Patent number
US03989681

Reaction notes

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