1-Bromo-3-methylbutane → 2,4-Dioxo-1-(3-methylbut-1-yl)-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

HRID 375588Notes

Reaction equation

HRID 375588 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6](=[O:21])[CH2:5]1.[CH3:22][CH:23]([CH3:27])[CH2:24][CH2:25]Br>CN(C)C=O.O>[O:3]=[C:4]1[N:10]([CH2:25][CH2:24][CH:23]([CH3:27])[CH3:22])[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:6](=[O:21])[CH2:5]1

Participants

6

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 10824683N-Desmethyl Dechloro Clobazam

Product 1

HCID 106158322,4-Dioxo-1-(3-methylbut-1-yl)-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride 80% dispersion in oil (0.057 g) was added portionwise to a solution of 2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.40 g) in dry dimethylformamide (15 ml). The reaction mixture was cooled to 0° and stirred for 30 min, then a solution of 3-methyl-1-bromobutane (0.23 ml) in dry dimethylformamide (4 ml) was added and stirring continued for 2 h. The reaction mixture was then diluted with water (100 ml), extracted with ethyl acetate (3×100 ml), washed with brine (2×50 ml), dried and concentrated in vacuo to give an oil which was purified by flash -chromatography (eluting with CH-EA 60:40) to give the title compound as a white solid (0.44 g). T.l.c. CH-EA (1:1), Rf=0.36.

Workup

  1. temperatureThe reaction mixture was cooled to 0°
  2. stirringstirring
  3. waitcontinued for 2 h
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washwashed with brine (2×50 ml)
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by flash -chromatography (eluting with CH-EA 60:40)

Sources & evidence

ORD record
ord-ed93124693144b269c0017e52ba385e7
Source dataset
uspto-grants-1996_01
Patent number
US05486514

Reaction notes

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