Methanol → 3-Allyloxybenzamide

HRID 429159Notes

Reaction equation

HRID 429159 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

A 15 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.

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-f96a7e0786f44d57ab0fe569a00f6f26
Source dataset
uspto-grants-2001_11
Patent number
US06316455B1

Reaction notes

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