Methyl iodide → HCID 58418733, compound

HRID 557488Notes

Reaction equation

HRID 557488 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[CH2:21][C:20]([CH3:23])=[CH:19]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:24]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[CH3:24][N:11]([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[CH2:21][C:20]([CH3:23])=[CH:19]2)[S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58418752HCID 58418752, compound

Product 1

HCID 58418733HCID 58418733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 15.0 g (45.8 mmol) of 4-methyl-N-[2-(2-methyl-1H-inden-7-yl)ethyl]-benzenesulfonamide in 100 mL of dry DMF at room temperature, 22.4 g (68.7 mmol) of Cs2CO3 was added, followed by the dropwise addition of 10.0 g (70.4 mmol) of MeI over a 10 minute period. This mixture was stirred for 24 hours at 50° C. and then evaporated under vacuum. To the residue, 200 mL of water and 200 mL of dichloromethane were added. The organic layer was separated, and the aqueous layer was washed with 200 mL of dichloromethane. The combined organic extract was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent—dichloromethane). Yield, 14.1 g (90%) of white solid. This product was further used without an additional purification. 1H NMR (CDCl3): δ 7.50-7.55 (m, 2H, 2,6-H in p-tolyl), 7.15-7.20 (m, 2H, 3,5-H in p-tolyl), 7.04 (m, 1H, 5-H in indenyl), 7.01 (m, 1H, 6-H in indenyl), 6.78 (m, 1H, 4-H in indenyl), 6.36 (m, 1H, 3-H in indenyl), 3.08-3.18 (m, 6H, 1,1′-H in indenyl and CH2CH2), 2.69 (s, 3H, NMe), 2.67 (s, 3H, 4-Me in p-tolyl), 2.05 (s, 3H, 2-Me in indenyl). Anal. Calc. for C20H23NO2S: C, 70.35; H, 6.79; N, 4.10%. Found: C, 70.95; H, 7.13; N, 3.78%.

Workup

  1. customevaporated under vacuum
  2. additionTo the residue, 200 mL of water and 200 mL of dichloromethane were added
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with 200 mL of dichloromethane
  5. extractionThe combined organic extract
  6. customwas evaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent—dichloromethane)
  8. customYield
  9. customThis product was further used without an additional purification

Sources & evidence

ORD record
ord-a0bf2680f19c4a148ded8936f1d6159e
Source dataset
uspto-grants-2011_11
Patent number
US08058461B2

Reaction notes

Loading…