Methyl iodide → 3-(4-Chlorophenyl)-1,4-dimethyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide

HRID 1245283Notes

Reaction equation

HRID 1245283 reaction equation
[C:1]([C:4]1([NH:10][S:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].[H-].[Na+].I[CH3:25]>CN(C=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[S:11](=[O:13])(=[O:12])[N:10]([CH3:25])[C:4]3([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[C:1]=2[CH3:2])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11461652N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamide

Product 1

HCID 113248403-(4-Chlorophenyl)-1,4-dimethyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxideYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

N-(1-Acetylcyclohexyl)-4-chlorophenylmethane sulfonamide (1.02 g, 3.1 mmol) was dissolved in dry DMF (10 mL) under Ar. NaH (60%, 2.2 eq.) and iodomethane (2 eq.) were added and the mixture was stirred overnight at 120° C. After dilution with water the solution was extracted with ethyl acetate. The organic layer was washed with NaCl solution and water, dried (Na2SO4) and concentrated to yield 696 mg (69%) of the 3-(4-chlorophenyl)-1,4-dimethyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide, shown below as a solid. MS (IS): 326 [MH]+.

Workup

  1. extractionAfter dilution with water the solution was extracted with ethyl acetate
  2. washThe organic layer was washed with NaCl solution and water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f9c9e13e5c1d4691b2a67b92135c7667
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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