Benzyl Bromide → HCID 21993944, compound

HRID 1978453Notes

Reaction equation

HRID 1978453 reaction equation
Cl.Cl.Cl.[N:4]1([CH2:11][CH2:12][CH2:13][NH:14][C:15]([CH:17]2[S:27][C:26]3[C:28]4[C:19]([CH:20]=[N:21][C:22]=4[N:23]=[CH:24][CH:25]=3)=[CH:18]2)=[O:16])[CH2:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>C(O)C.C(=O)([O-])O.[Na+]>[CH2:29]([N:7]1[CH2:8][CH2:9][CH2:10][N:4]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:17]2[S:27][C:24]3[N:23]4[C:19](=[CH:20][N:21]=[C:22]4[CH:28]=[CH:26][CH:25]=3)[CH:18]=2)=[O:16])[CH2:5][CH2:6]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 70247920HCID 70247920, compound

Product 1

HCID 21993944HCID 21993944, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In 10 ml of ethanol were suspended 606.9 mg (1.3 mM) of N-[3-(hexahydro-1,4-diazepin-1-yl)propan-1-yl]-5-thia-1,8-diazaacenaphthylene-4-carboxamide trihydrochloride and 342.1 mg (2.0 mM) of benzyl bromide, followed by addition of 0.91 ml (6.5 mM) of triethylamine, and the mixture was refluxed overnight. This reaction mixture was diluted with 5% aqueous solution of sodium hydrogen carbonate and and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over Na2SO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=2/3) to provide the title compound as deep-red liquid (320.0 mg, 55.0%).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over Na2SO4
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=2/3)

Sources & evidence

ORD record
ord-c7f785aedf9843228dd6058b7088f9a2
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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