Benzyl Bromide → HCID 15452009, compound

HRID 1197288Notes

Reaction equation

HRID 1197288 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([NH:16][NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)C>[C:18]([N:17]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[NH:16][C:14]([C:10]1[O:9][CH:13]=[CH:12][CH:11]=1)=[O:15])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15452036HCID 15452036, compound

Product 1

HCID 15452009HCID 15452009, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (1.8 g), 1-furoyl-2-t-butyl hydrazine (2 g) and excess powdered potassium carbonate were stirred in dimethylformamide (50 ml) at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with diethyl ether and washed several times with water. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed in vacuo. The white solid product was chromatographed on silica gel (G:70°-230 mesh) using methylene chloride as eluent to afford the product in good yield: m.p. 152°-153.

Workup

  1. washwashed several times with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe white solid product was chromatographed on silica gel (G:70°-230 mesh)
  6. customto afford the product in good yield

Sources & evidence

ORD record
ord-77696815a3c64cdfb2ab584a2065c951
Source dataset
uspto-grants-1992_05
Patent number
US05117057

Reaction notes

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