Methyl iodide → Methyl 5-Iodo-2-(methyl(methylsulfonyl)amino)benzoate

HRID 1070649Notes

Reaction equation

HRID 1070649 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:17]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11552135Methyl 5-iodo-2-(methylsulfonamido)benzoate

Product 1

HCID 22397180Methyl 5-Iodo-2-(methyl(methylsulfonyl)amino)benzoateYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-iodo-2-((methylsulfonyl)amino)benzoate (Preparation 49, 0.50 g) and K2CO3 (0.41 g) in DMF (10 mL) is added iodomethane (0.10 mL) at ambient temperature. After 24 hrs, the solvent is removed in vacuo and the residue is partitioned between Et2O (20 mL) and water (20 mL). The organic layer is separated, dried over MgSO4, filtered, and concentrated in vacuo. The crude yellow liquid is purified by silica gel column chromatography (4/1, hexanes/EtOAc) to afford 0.48 g (92%) of the title compound as a white solid. Physical characteristics: m.p. 105-106° C.; 1H NMR (300 MHz, CDCl3) δ8.22, 7.86, 7.18, 3.91, 3.27, 2.96; IR (diffuse reflectance) 1718, 1443, 1330, 1289, 1258, 1150, 1056, 970, 964, 957, 888, 839, 772, 732, 712 cm−1; MS (ESI+) m/z 370 (MH+). Anal. Found: C, 32.74; H, 3.30; N, 3.81.

Workup

  1. customthe solvent is removed in vacuo
  2. customthe residue is partitioned between Et2O (20 mL) and water (20 mL)
  3. customThe organic layer is separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude yellow liquid is purified by silica gel column chromatography (4/1, hexanes/EtOAc)

Sources & evidence

ORD record
ord-2f330eaf56ef4bde9e4a1758ebd01a43
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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