Methyl iodide → HCID 3844902, compound

HRID 472486Notes

Reaction equation

HRID 472486 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH3:2].[C:17](=O)([O-])[O-].[Cs+].[Cs+].IC>C(#N)C.ClCCl>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]([S:12]([CH3:15])(=[O:13])=[O:14])[CH3:17])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 706844Ethyl 2-methanesulfonamidobenzoate

Product 1

HCID 3844902HCID 3844902, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

195 b) To a stirred suspension of 2-methanesulfonylamino-benzoic acid ethyl ester (1.0 g, 4.1 mmol) and cesium carbonate (1.5 g, 4.5 mmol) in acetonitrile (10 mL) was added iodomethane (0.28 mL, 4.5 mmol). The mixture was stirred at room temperature for 18 hours then diluted with dichloromethane (30 mL), filtered through a plug of diatomaceous earth and evaporated. 2-(Methanesulfonyl-methyl-amino)-benzoic acid ethyl ester was isolated as a clear viscous oil (1.08 g, 100%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.90 (d, J=7.7 Hz, 1H), 7.55 (t, J=7.7 Hz, 1H), 7.47-7.38 (m, 2H), 4.38 (q, J=7.0 Hz, 2H), 3.32 (s, 3H), 2.96 (s, 3H), 1.41 (t, J=7.1 Hz, 3H). MS=280 (M+Na)+.

Workup

  1. filtrationfiltered through a plug of diatomaceous earth
  2. customevaporated

Sources & evidence

ORD record
ord-a306ee41d1cd47eea9cceaffb1c26f0e
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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