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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamide	HCID 11461652	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-(4-Chlorophenyl)-4-methyl-2-thia-1-azaspiro[4.5]dec-3-ene	HCID 21910643	71.1%

Reaction Conditions

Temperature	120 °C

Reaction Steps

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]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07125840B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-0d6727f5bae64d31851d21506fffeff3
Source note	uspto-grants-2006_10