Methanol → 3-Allyloxybenzamide

HRID 850051Notes

Reaction equation

HRID 850051 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19].CO>C(#N)C.C(Cl)Cl>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])[CH:18]=[CH2:17]

Participants

7

Reactant 4

HCID 887MethanolHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 3424033-Hydroxybenzamide

Product 1

HCID 183546133-Allyloxybenzamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-hydroxybenzamide (274 mg; 2.0 mM) under a nitrogen atmosphere was added potassium carbonate (276 mg; 21.0 mM). This was dissolved in acetonitrile (20 ml) containing allyl bromide (169 ul; 2.0 mM). The mixture was refluxed for 5 hours, and the reaction followed by T.L.C.: 10% MeOH: 90% CH2Cl2. The excess solvent was then removed under vacuum, the organics extracted into dichloromethane, dried, and the solvent removed, to yield a white solid. This was recrystallised from hot water to produce a white "needle" solid (63%) as the final product. Melting point: 116-117° C. 1H NMR: δ=4.7(m;2H:He,Hf); 5.5(m;2H;Hh,Hi); 6.2(m;1H;Hg); 7.2(m;1H;Hd); 7.6m;4H;Ha,Hb,Hc,NH); 8.1(s;1H;NH). 13C NMR: δ=68.580, 113.821, 117.978, 129.661, 133.893, 136.025, 158.371, 167.892. Mass spectra: EI: 177 (M+); 41 (100%)

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customThe excess solvent was then removed under vacuum
  3. extractionthe organics extracted into dichloromethane
  4. customdried
  5. customthe solvent removed
  6. customto yield a white solid
  7. customThis was recrystallised from hot water

Sources & evidence

ORD record
ord-1e6a3926ea314586b0bbcbb3641827cc
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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