Benzyl Bromide → HCID 178518536, compound

HRID 2222580Notes

Reaction equation

HRID 2222580 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[NH:15][C:14](=[S:16])[NH:13][C:12]2=[O:17])=[CH:2]1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[OH-].[Na+].CO>[CH2:18]([S:16][C:14]1[NH:13][C:12](=[O:17])/[C:11](=[CH:10]/[C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)/[N:15]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178518550HCID 178518550, compound

Product 1

HCID 178518536HCID 178518536, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-2-thioxoimidazolidin-4-one (500 mg, 2.05 mmol) in 12.6% aq. NaOH (1 mL) and methanol (5 mL), benzyl bromide (430 mg, 2.5 mmol) was added and the reaction mixture stirred at RT for 18 h. Most of the solvent was distilled out and the precipitate was filtered and washed first with water, then with diethylether and dried. The crude material was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 15:1). Obtained the desired (5Z)-2-(benzylthio)-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-3,5-dihydro-4H-imidazol-4-one, as a yellow solid (700 mg, 2 mmol).

Workup

  1. distillationMost of the solvent was distilled out
  2. filtrationthe precipitate was filtered
  3. washwashed first with water
  4. dry with materialwith diethylether and dried
  5. customThe crude material was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 15:1)

Sources & evidence

ORD record
ord-0c7a28345d734ba290ae1ecfb3edc8bf
Source dataset
uspto-grants-2008_05
Patent number
US07371862B2

Reaction notes

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