Sodium Hydroxide → 2-(2-(3,4-Dichloro-N-methylphenylsulfonamido)phenyl)-acetic acid

HRID 1642119Notes

Reaction equation

HRID 1642119 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([CH3:23])[S:12]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)(=[O:14])=[O:13].CO.O1CCOCC1.[OH-].[Na+]>>[Cl:22][C:17]1[CH:16]=[C:15]([S:12]([N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][C:3]([OH:24])=[O:2])[CH3:23])(=[O:13])=[O:14])[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21966525Dioxane MethanolHCID 667559532-(2-(3,4-Dichloro-N-methylphenylsulfonamido)phenyl)-acetic acid methyl ester

Product 1

HCID 667562712-(2-(3,4-Dichloro-N-methylphenylsulfonamido)phenyl)-acetic acid

Procedure

2-(2-(3,4-Dichloro-N-methylphenylsulfonamido)phenyl)acetic acid methyl ester (13.7 g, 34.26 mmol) was dissolved in a mixture of methanol/dioxane/4 M NaOH (15/4/1) (266 ml, 52.92 mmol NaOH), and then further 4 M NaOH (39.7 ml, 158.76 mmol) was added. The resulting clear solution was stirred overnight at room temperature and then concentrated in vacuo. The residue was taken up in ethyl acetate and washed with 0.5 M KHSO4. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution, dried over sodium sulfate and concentrated.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with 0.5 M KHSO4
  3. extractionThe aqueous phase was then extracted several times with ethyl acetate
  4. washThe combined organic phases were washed with saturated NaCl solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a87b6cf80184a078506a32699dda601
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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