Carzenide → prop-2-enyl 4-sulfamoylbenzoate

HRID 2086144Notes

Reaction equation

HRID 2086144 reaction equation
[S:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].C(=O)(O)[O-].[Na+].[CH2:19](I)[CH:20]=[CH2:21]>CN(C=O)C>[CH2:21]([O:10][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([S:1](=[O:3])(=[O:4])[NH2:2])=[CH:13][CH:12]=1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 8739CarzenideHCID 11166Allyl iodideHCID 516892Sodium Bicarbonate

Product 1

HCID 11536043prop-2-enyl 4-sulfamoylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-Sulfamoyl-benzoic acid (2.0 g, 9.94 mmol) and sodium bicarbonate (0.84 g, 9.94 mmol) in DMF (20 mL) was added allyl iodide (0.91 mL, 9.94 mmol) and stirred at room temperature overnight under argon. The reaction was quenched with water, extracted with EtOAc and dried over Na2SO4. After removing the solvent under reduced pressure, the crude product was used in the next reaction without further purification. 1H NMR (400 MHz, CDCl3) δ8.20 (d, 2H), 8.00 (d, 2H), 6.06 (m, 1H), 5.40 dd, 2H), 5.02 (s, 2H), 4.96 (d, 2H). MH+ 243.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent under reduced pressure
  5. customthe crude product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-c0e1b01567e545df86696575e3a4173c
Source dataset
uspto-grants-2004_04
Patent number
US06723749B2

Reaction notes

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