Water → HCID 4349311, compound

HRID 1064336Notes

Reaction equation

HRID 1064336 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9].I[CH3:19].O>C1COCC1>[CH3:3][O:4][CH2:5][CH2:6][N:7]([CH3:19])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1587718HCID 1587718, compound

Product 1

HCID 4349311HCID 4349311, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (144 mg, 3.6 mmol) was added in portions to a solution of N-(2-methoxyethyl)-4-iodobenzenesulphonamide (Method 40, 1 g, 3 mmol) in THF (10 ml) and the mixture stirred at ambient temperature for 15 minutes. Iodomethane (230 μl, 3.6 mmol) was added and the reaction stirred for 18 hours. Water (30 ml) was added cautiously and the mixture extracted with ether (40 ml). The combined organics were washed with brine (50 ml), dried and the volatiles evaporated. The residue was purified by flash chromatography on silica gel eluting with iso-hexane/EtOAc (100:0 increasing in polarity to 10:1) to give the title compound (730 mg, 69%) as a clear oil. NMR 2.78 (s, 3H), 3.16 (t, 2H), 3.22 (s, 3H), 3.45 (t, 3H), 7.42 (d, 2H), 7.80 (d, 2H); m/z 356.

Workup

  1. stirringthe reaction stirred for 18 hours
  2. extractionthe mixture extracted with ether (40 ml)
  3. washThe combined organics were washed with brine (50 ml)
  4. customdried
  5. customthe volatiles evaporated
  6. customThe residue was purified by flash chromatography on silica gel eluting with iso-hexane/EtOAc (100:0 increasing in polarity to 10:1)

Sources & evidence

ORD record
ord-7a461bacb47b497783b198233148f75d
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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