Water → 3-(4-Chlorophenyl)-4-methyl-2-thia-1-azaspiro[4.5]dec-3-ene

HRID 1245284Notes

Reaction equation

HRID 1245284 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)=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].[H-].[Na+].O>CN(C=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[S:11][NH:10][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 962WaterHCID 24758Sodium hydrideHCID 11461652N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamide

Product 1

HCID 219106433-(4-Chlorophenyl)-4-methyl-2-thia-1-azaspiro[4.5]dec-3-eneYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To N-(1-acetylcyclohexyl)-(4-chlorophenyl)methane-sulfonamide (612 mg, 1.86 mmol), from Example 1, in dry DMF (6 mL) was added NaH (60%, 2.2 eq.) under Ar. The mixture was stirred overnight at 120° C., water was added and the solution was extracted with ethyl acetate. The organic layer was washed with NaCl solution and water, dried (Na2SO4) and concentrated. Recrystallization from ethyl acetate yielded 0.37 g (64%) of 3-(4-chlorophenyl)-4-methyl-2-thia-1-azaspiro[4.5]dec-3-ene, 2,2-dioxide, shown below as a solid. MS (IS): 312 [MH]+

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with NaCl solution and water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-0d6727f5bae64d31851d21506fffeff3
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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