Benzyl Bromide → HCID 19769112, compound

HRID 2081535Notes

Reaction equation

HRID 2081535 reaction equation
[C:1]([C:3]1[C:4](=[O:20])[NH:5][C:6]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([CH2:9][CH3:10])[CH:8]=1)#[N:2].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Al]>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:21]([O:20][C:4]1[C:3]([C:1]#[N:2])=[CH:8][C:7]([CH2:9][CH3:10])=[C:6]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 5359268AluminumHCID 19769113HCID 19769113, compound

Product 1

HCID 19769112HCID 19769112, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalyst2×HCID 241BenzeneSolvent

Procedure

To a partial suspension of 3-cyano-5-ethyl-6-benzyloxymethyl-2(1H)-pyridinone (1.36 g, 5.08 mmol) in dry benzene (20 mL) was added benzyl bromide (0.80 mL, 6.7 mmol) and then silver carbonate (1.43 g, 5.2 mmol). This mixture was covered with aluminum foil and allowed to stir at room temperature. After 24 hours, the reaction was estimated to be ~80% complete. Additional silver carbonate (0.40 g, 1.45 mmol) was added and the mixture was stirred for another 24 hours until complete. The silver salts were removed by filtration, rinsed with benzene and the combined benzene washings were evaporated to give the pure product as an oil.

Workup

  1. stirringthe mixture was stirred for another 24 hours until complete
  2. customThe silver salts were removed by filtration
  3. washrinsed with benzene
  4. customthe combined benzene washings were evaporated

Sources & evidence

ORD record
ord-3fea9745d05d4acb9bd5e99286fb2f27
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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