Phenethyl bromide → 2,4-Dioxo-5-phenyl-1-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

HRID 1683324Notes

Reaction equation

HRID 1683324 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.[C:22]1([CH2:28][CH2:29]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.CC(=O)OCC>[O:3]=[C:4]1[N:10]([CH2:29][CH2:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[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 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 10824683N-Desmethyl Dechloro Clobazam

Product 1

HCID 105944392,4-Dioxo-5-phenyl-1-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride 80% dispersion in oil (0.13 g) was added portionwise to a solution of the 2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (compound a) (1 g) in DMF (18 ml) previously cooled at 0°. The reaction was stirred for 20 min at 0°, then a solution of 2-phenylethyl bromide (0.85 ml) in DMF (2 ml) was added dropwise, the mixture was stirred at 23° for 15 h, then diluted with EA (80 ml) and washed with brine (3×100 ml), dried and concentrated "in vacuo". The crude product was purified by flash chromatography (eluting with CH-EA 1:1) to give the title compound as a white powder (0.85 g). T.l.c. CH-EA (1:1), Rf =0.27.

Workup

  1. temperaturepreviously cooled at 0°
  2. stirringthe mixture was stirred at 23° for 15 h
  3. washwashed with brine (3×100 ml)
  4. customdried
  5. concentrationconcentrated "in vacuo"
  6. customThe crude product was purified by flash chromatography (eluting with CH-EA 1:1)

Sources & evidence

ORD record
ord-2a403e99efa64ba29e5dd117948b6de8
Source dataset
uspto-grants-1997_06
Patent number
US05637697

Reaction notes

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