Water → HCID 59750944, compound

HRID 748770Notes

Reaction equation

HRID 748770 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH2:12][CH2:13][NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:31].O>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH2:12][CH2:13][N:14]([CH3:31])[C:15](=[O:19])[O:16][CH2:17][CH3:18])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 59750703HCID 59750703, compound

Product 1

HCID 59750944HCID 59750944, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In tetrahydrofuran (4 ml) was dissolved ethyl N-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propyl]carbamate (100 mg, 0.239 mmol), followed by the addition of sodium hydride (60% dispersion in mineral oil, 11.5 mg, 0.287 mmol). The resulting mixture was stirred at room temperature for 3 hours. Iodomethane (17.8 μl, 0.287 mmol) was added and the mixture was stirred at room temperature for 15 hours. Sodium hydride (60% dispersion in mineral oil, 5.00 mg, 0.125 mmol) and iodomethane (10.0 μl, 0.161 mmol) were added, followed by stirring at room temperature for 24 hours. Water (5 ml) was added, and the mixture was concentrated. The residue thus obtained was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated, whereby the title compound (83.2 mg, 0.193 mmol, 81%) was obtained as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hours
  2. stirringby stirring at room temperature for 24 hours
  3. concentrationthe mixture was concentrated
  4. customThe residue thus obtained
  5. extractionwas extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. concentrationethyl acetate=3:1 eluate was concentrated

Sources & evidence

ORD record
ord-510866597b0f4153bdd06a6e56e298f2
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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