Sodium Bicarbonate → 5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 354776Notes

Reaction equation

HRID 354776 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:15]([CH3:32])[C:16]([C:18]([NH:21]C(=O)OCC1C=CC=CC=1)([CH3:20])[CH3:19])=[O:17])=O.C(=O)(O)[O-].[Na+]>Br>[F:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]1[C:6]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=2[N:15]([CH3:32])[C:16](=[O:17])[C:18]([CH3:20])([CH3:19])[N:21]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86738817HCID 86738817, compound

Product 1

HCID 205061565-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 20 mg (0.04 mol) of benzyl [1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]-methylcarbamoyl]-1-methylethyl]carbamate in 0.5 ml of hydrogen bromide/glacial acetic acid (30 percent) is left to stand for 15 minutes, subsequently treated with a 10 percent sodium bicarbonate solution and extracted several times with methylene chloride. The organic phase is dried over sodium sulphate and concentrated, whereupon the residue is chromatographed on a pressure column containing 2 g of silica gel (particle size 0.04-0.06 mm) under 0.2-0.4 atmospheres of nitrogen with methylene chloride as the elution agent. By crystallisation from ether/petroleum ether there is obtained 5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 127°-129°.

Workup

  1. extractionextracted several times with methylene chloride
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated, whereupon the residue
  4. customis chromatographed on a pressure column
  5. additioncontaining 2 g of silica gel (particle size 0.04-0.06 mm) under 0.2-0.4 atmospheres of nitrogen with methylene chloride as the elution agent
  6. customBy crystallisation from ether/petroleum ether there

Sources & evidence

ORD record
ord-d785fabd25df485880116b8a8225ebc6
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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