Methyl iodide → Methyl 2-{methyl[(4-methylphenyl)sulfonyl]amino}acetate

HRID 81861Notes

Reaction equation

HRID 81861 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.O>[CH3:17][N:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetate

Product 1

HCID 3277444Methyl 2-{methyl[(4-methylphenyl)sulfonyl]amino}acetateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 2-(4-methylphenylsulfonamido)acetate (3.10 g, 12.8 mmol) and Cs2CO3 (8.31 g, 25.5 mmol) in DMF (0.1 M) was added MeI (877 μL, 14.1 mmol). The reaction was allowed to stir overnight at rt. The reaction was then diluted with water and repeatedly extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to furnish 6 (2.80 g, 85%): δH (400 MHz, CDCl3) 2.42 (s, 3H, CH3), 2.87 (s, 3H, CH3), 3.66 (s, 3H, CH3), 3.97 (s, 2H, CH2), 7.31 (d, J=8.4 Hz, 2H, CH), 7.69 (d, J=8.4 Hz, 2H, CH); LRMS (ES+) calcd for [C11H15NO4S+H] 258.08. found 258.06 [M+H].

Workup

  1. extractionrepeatedly extracted with CH2Cl2
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4b828cd64a8417780dcb6b0c0dc101b
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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