Methyl iodide → HCID 19107600, compound

HRID 1646530Notes

Reaction equation

HRID 1646530 reaction equation
[H-].[Na+].[C:3]1([CH:9]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][Br:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:29]I.[Cl-].[NH4+]>C1COCC1>[CH3:29][N:17]([CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[S:18]([C:21]1[CH:22]=[CH:23][C:24]([CH2:27][Br:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19107610HCID 19107610, compound

Product 1

HCID 19107600HCID 19107600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil: 190 mg, 4.7 mmol) was added to a stirred solution of N-1,2-diphenylethyl 4-bromomethylbenzenesulphonamide (2.00 g, 4.7 mmol) in dry THF (50 ml) at 0° C. under argon. Methyl iodide (0.6 ml, 9.3 mmol) was added immediately to the reaction mixture. The mixture was stirred for 48 h at ambient temperature. Saturated aqueous ammonium chloride (50 ml) was added and the mixture extracted with ethyl acetate (2×80 ml). The combined organics were washed with brine (50 ml), dried over anhydrous sodium sulphate, filtered and concentrated to give N-methyl-N-1,2-diphenylethyl 4-bromomethylbenzenesulphonamide as an orange oil which was used directly in the next step.

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×80 ml)
  2. washThe combined organics were washed with brine (50 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-550c4a5e179f4878967440ee47849a6f
Source dataset
uspto-grants-1993_01
Patent number
US05180723

Reaction notes

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