Acetone → HCID 67330236, compound

HRID 503099Notes

Reaction equation

HRID 503099 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-b773556f58a44928a65b3c901c68f6cf
Source dataset
uspto-grants-2010_08
Patent number
US07776909B2

Reaction notes

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