Methanol → {4-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-benzoylamino}-acetic acid

HRID 446858Notes

Reaction equation

HRID 446858 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][NH:6][C:7](=[O:33])[C:8]1[CH:13]=[CH:12][C:11]([S:14](=[O:32])(=[O:31])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[CH:10][CH:9]=1)C.O.CO>O1CCCC1>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][S:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][C:4]([OH:34])=[O:3])=[O:33])=[CH:9][CH:10]=1)(=[O:31])=[O:32]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 68494934HCID 68494934, compound

Product 1

HCID 68493493{4-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-benzoylamino}-acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {4-[2-(2,4-dichloro-phenoxy)-phenylsulfamoyl]-benzoylamino}-acetic acid ethyl ester (7.68 g, 14.67 mmol) in a mixture of tetrahydrofuran (36 mL), water (18 mL) and methanol (18 mL) lithium hydroxide monohydrate (3.09 g, 73.64 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated, the residue was dissolved in water, acidified with 1M hydrochloric acid, the precipitated solid was filtered off, washed with water and dried to yield 6.76 g (93%) of the title compound as a yellowish solid. MS (EI) 496.2 (MH+).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in water
  4. filtrationthe precipitated solid was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-78b286e9214246a0adcbb984ffcb41ea
Source dataset
uspto-grants-2013_07
Patent number
US08481527B2

Reaction notes

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