Acetone → HCID 67330236, compound

HRID 240823Notes

Reaction equation

HRID 240823 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[CH3:12].CC(C)=O.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])=[CH:7][C:6]=1[CH3:12]

Participants

4

Reactant 3

HCID 180AcetoneHCID 7369Benzenesulfonyl chlorideHCID 21876486HCID 21876486, compound

Product 1

HCID 67330236HCID 67330236, compoundYield 94.3%

Procedure

To a solution of 2-methyl-4-amino phenylacetic acid methyl ester (5.3 mmol) in acetone (10 mL) dry pyridine (7.95 mmol) and phenylsulfonyl chloride (6.36 mmol) have been added and the resulting solution has been left stirring overnight at room temperature. Acetone has been evaporated and the residue diluted with CHCl3 (15 mL), washed with 1N HCl (2×10 mL), water (3×20 mL), dried over Na2SO4 and evaporated under vacuum to give {2-methyl-4-[(phenylsulphonyl)amino]phenyl}acetic acid methyl ester as colourless oil (5.0 mmol) pure to be used in the following reaction. Following the procedure described for Example 1 and starting from the methyl ester (5.0 mmol) pure {2-methyl-4-[(phenylsulphonyl)amino]phenyl}acetic acid has been synthesised (4.75 mmol).

Workup

  1. waitthe resulting solution has been left
  2. customAcetone has been evaporated
  3. additionthe residue diluted with CHCl3 (15 mL)
  4. washwashed with 1N HCl (2×10 mL), water (3×20 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-7678bc11b76247b6b144d498a885f278
Source dataset
uspto-grants-2014_02
Patent number
US08648110B2

Reaction notes

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