Acetone → HCID 21529391, compound

HRID 1658440Notes

Reaction equation

HRID 1658440 reaction equation
C([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[N+:7]([O-:23])[CH2:6][C:5]1=[O:24])C=C.[Mn]([O-])(=O)(=O)=[O:26].[K+].[CH3:31][C:32]([CH3:34])=[O:33]>O>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]2[N:4]([CH2:31][CH:32]([OH:33])[CH2:34][OH:26])[C:5](=[O:24])[CH2:6][N+:7]([O-:23])=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:9]=2[CH:14]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 21529377HCID 21529377, compound

Product 1

HCID 21529391HCID 21529391, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.3 g of 1-allyl-7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide are dissolved in acetone and treated dropwise with a solution of 1.6 g of potassium permanganate in water. After the addition, the mixture is stirred for a further 25 minutes at room temperature. Then the mixture is filtered off under vacuum from manganese dioxide, whereupon the manganese dioxide is washed with acetone and the filtrate is freed from acetone on a rotary evaporator. The aqueous phase is extracted with ethyl acetate and the organic phase is washed with water, concentrated and dried azeotropically with benzene. By chromatography on silica gel with ethyl acetate/methanol (9:1) there is isolated from the residue 7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide. For analysis, a sample is recrystallized from ethyl acetate; melting point 165°-166°C.

Workup

  1. additionAfter the addition
  2. filtrationThen the mixture is filtered off under vacuum from manganese dioxide, whereupon the manganese dioxide
  3. washis washed with acetone
  4. customthe filtrate is freed from acetone on a rotary evaporator
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. washthe organic phase is washed with water
  7. concentrationconcentrated
  8. dry with materialdried azeotropically with benzene

Sources & evidence

ORD record
ord-5176d1207e36477f97b397aec3c710ec
Source dataset
uspto-grants-1976_06
Patent number
US03963777

Reaction notes

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