Water → 4-[(2-methylsulfonyl-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide

HRID 1789662Notes

Reaction equation

HRID 1789662 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][CH2:9][CH2:10][N:11]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][CH2:22][CH3:23])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH2:32]>CO>[CH3:7][S:8]([CH2:9][CH2:10][N:11]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)[C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:21][CH2:22][CH3:23])(=[O:19])=[O:20])=[CH:16][CH:17]=1)(=[O:1])=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 220362154-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 220361614-[(2-methylsulfonyl-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Oxone® (0.54 g, 0.88 mmol) in H2O (2 mL) was added to a 0° C. solution of 4-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide (0.13 g, 0.34 mmol) in MeOH (8 mL) resulting in an immediate precipitate. After 1 h, the mixture was partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 (2×). The combined organic layer was dried (Na2SO4), filtered, and evaporated in vacuo to afford 0.14 g (100%) of 4-[(2-methylsulfonyl-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide as a pale glass; (m+H)+ 415.

Workup

  1. customresulting in an immediate precipitate
  2. customthe mixture was partitioned between CH2Cl2 and H2O
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-cc91ba7f425e451d989228df5b9a3e76
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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