Water → HCID 18183217, compound

HRID 430669Notes

Reaction equation

HRID 430669 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[C:12]4[O:17][CH2:16][O:15][C:13]4=[CH:14][C:8]=3[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][N:5]2[C:24]=1[CH3:25].C([Li])CCC.CN(C)[CH:33]=[O:34].O>O1CCCC1>[CH:33]([C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[C:12]4[O:17][CH2:16][O:15][C:13]4=[CH:14][C:8]=3[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:6][N:5]2[C:24]=1[CH3:25])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 18183192HCID 18183192, compoundHCID 178418339Butyllithium

Product 1

HCID 18183217HCID 18183217, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

120 mg of 9-bromo-8-methyl-5-phenyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine is mixed in 15 ml of tetrahydrofuran at −78° C. with 0.36 ml of butyllithium (hexane, 1 mol) and stirred for 15 minutes. It is then mixed at this temperature with 0.6 ml of dimethylformamide and stirred for 15 minutes. After stirring to room temperature, it is mixed with water, the tetrahydrofuran is distilled off and extracted with ethyl acetate. After the solvent is distilled off, it is chromatographed on silica gel with dichloromethane:ethanol=95:5 as an eluant. 46 mg of 9-formyl-8-methyl-5-phenyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine is obtained.

Workup

  1. stirringstirred for 15 minutes
  2. stirringAfter stirring to room temperature
  3. distillationthe tetrahydrofuran is distilled off
  4. extractionextracted with ethyl acetate
  5. distillationAfter the solvent is distilled off
  6. customit is chromatographed on silica gel with dichloromethane

Sources & evidence

ORD record
ord-e2a7a86813ce49df9d870252d1013fb0
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

Loading…