Toluene → 5-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-2h-1,4-benzodiazepin-2-one

HRID 437334Notes

Reaction equation

HRID 437334 reaction equation
C(OC(=O)[NH:10][CH:11]([C:13](=[O:33])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[C:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[CH3:12])C1C=CC=CC=1.C1(C)C=CC=CC=1>C(O)(=O)C>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:24]1[C:16]2[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=2[NH:14][C:13](=[O:33])[CH:11]([CH3:12])[N:10]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 20443633(-)-Benzyl-[1-[{2-(o-chlorobenzoyl)4-nitrophenyl}carbamoyl]-ethyl]carbamate

Product 1

HCID 933645-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-2h-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

35 g of the foregoing propionoanilide are heated to reflux in 40 ml of glacial acetic acid and 200 ml of absolute toluene for 15 minutes. The residue obtained after distillation of the solvent is treated with methylene chloride and 10% sodium bicarbonate solution. The methylene chloride solution is washed twice with 10% sodium bicarbonate solution and once with water, dried over sodium sulfate, filtered and concentrated. The residue is taken up in benzene, some racemate formed crystallising out and being filtered off. The benzene solution is evaporated and the residue crystallised from ether to give (+)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one which melts at 198°-200° C and exhibits a rotation of [α]25D =+252.1° (in methylene chloride, 1%).

Workup

  1. customThe residue obtained
  2. distillationafter distillation of the solvent
  3. additionis treated with methylene chloride and 10% sodium bicarbonate solution
  4. washThe methylene chloride solution is washed twice with 10% sodium bicarbonate solution and once with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customsome racemate formed
  9. customcrystallising out
  10. filtrationbeing filtered off
  11. customThe benzene solution is evaporated
  12. customthe residue crystallised from ether

Sources & evidence

ORD record
ord-2c0ae86369cd486780fd2cd5a093dc48
Source dataset
uspto-grants-1977_06
Patent number
US04031078

Reaction notes

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