Benzyl Bromide → HCID 24851706, compound

HRID 500548Notes

Reaction equation

HRID 500548 reaction equation
[CH3:1][S:2]([C:5]1[N:6]([CH3:17])[C:7]([C:10]2[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=2)=[N:8][N:9]=1)(=[O:4])=[O:3].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=O)([O-])[O-].[Ag+].[Ag+]>[CH2:18]([O:16][C:12]1[CH:11]=[C:10]([C:7]2[N:6]([CH3:17])[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[N:9][N:8]=2)[CH:15]=[CH:14][N:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 24851813HCID 24851813, compound

Product 1

HCID 24851706HCID 24851706, compound

Reagents, catalysts & solvents 1

HCID 92796Silver carbonateCatalyst

Procedure

The title compound from example 27.1 (0.95 g, 3.7 mmol) and silver (1) carbonate (1.23 g, 4.48 mmol) were combined in a round bottom flask and purged with nitrogen. Toluene (10 mL) was added, followed by benzyl bromide (0.53 mL, 4.48 mmol) and the reaction was stirred for 72 h at room temperature. The silver salts were then removed by filtration through diatomaceous earth, which were then washed with dichloromethane. The filtrate was concentrated then purified by column chromatography on silica gel with 0-10% ethyl acetate in dichloromethane to give the title compound (off-white solid, 549 mg, 43

Workup

  1. custompurged with nitrogen
  2. additionToluene (10 mL) was added
  3. customThe silver salts were then removed by filtration through diatomaceous earth, which
  4. washwere then washed with dichloromethane
  5. concentrationThe filtrate was concentrated
  6. customthen purified by column chromatography on silica gel with 0-10% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-c594830b7e894e8e818b093cfa0ed23e
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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