Sodium Hydroxide → HCID 11670217, compound

HRID 855988Notes

Reaction equation

HRID 855988 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:35])[C:6]1[CH:11]=[C:10]([S:12](=[O:33])(=[O:32])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:7]=1[CH3:34]>CO>[CH3:34][C:7]1[CH:8]=[CH:9][C:10]([S:12](=[O:33])(=[O:32])[NH:13][C:14]2[CH:15]=[CH:16][C:17]([S:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:18][CH:19]=2)=[CH:11][C:6]=1[C:5]([OH:35])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58937034HCID 58937034, compound

Product 1

HCID 11670217HCID 11670217, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.0N aqueous sodium hydroxide (9.1 ml, 9.16 mmol) was added to a solution of 2-methyl-5-[4-(4-trifluoromethyl-benzylsulfanyl)-phenylsulfamoyl]-benzoic acid methyl ester (1.13 g, 2.29 mmol) in 100 ml methanol and the resulting solution was heated at reflux overnight under nitrogen. The reaction solution was then cooled to room temperature and concentrated under reduced pressure. The residue was stirred in 1.0N aqueous hydrochloric acid solution (25 ml) and filtered to yield the title compound as a white solid (1.03 g, 94% yield). MS: 480.2 (M−1); 1H NMR (400 MHz, CD3OD): δ2.49 (s, 3H), 4.04 (s, 2H), 6.96 (d, 2H), 7.1 (d, 2H), 7.29 (m, 2H), 7.33 (d, 1H), 7.47 (m, 3H), 7.94 (b, 1H).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux overnight under nitrogen
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered

Sources & evidence

ORD record
ord-82bd0a81e6d2451e88ddb4f8ca1607bb
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Reaction notes

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