Allyl bromide → 4-Acetamidosalicylic acid allyl ester

HRID 1681584Notes

Reaction equation

HRID 1681584 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:8]=[C:9]([OH:16])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=[O:12])(=[O:5])[CH3:4].[H][H].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C=O)C>[CH2:21]([O:12][C:11](=[O:13])[C:10]1[C:9](=[CH:8][C:7]([NH:6][C:3](=[O:5])[CH3:4])=[CH:15][CH:14]=1)[OH:16])[CH:20]=[CH2:19]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 655094-Acetamidosalicylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 539592554-Acetamidosalicylic acid allyl esterYield 62,745.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (4.0 g of 60%, 0.1 mmol) in 25 mL DMF was added dropwise a solution of 4-acetamidosalicylic acid (19.5 g, 0.1 mmol) in 50 mL DMF. After the evolution of hydrogen was over, allyl bromide (12.1 g, 0.1 mmol) was added and the mixture was stirred for 8.6 hours. DMF was removed in vacuo and the residue crystallized from methanol/water to give 14.76 g (62.76%) of the title compound as a white solid, mp 156-8° C.

Workup

  1. additionwas added
  2. customDMF was removed in vacuo
  3. customthe residue crystallized from methanol/water

Sources & evidence

ORD record
ord-4ba4528ef2f64ac7ac8a794d6d9a3d7f
Source dataset
uspto-grants-1992_12
Patent number
US05173486

Reaction notes

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