Dichloromethane → N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

HRID 2188543Notes

Reaction equation

HRID 2188543 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[C:12]2([CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1.ClCCl.C1COCC1>[O-]S([O-])(=O)=O.[Cu+2].O1CCOCC1>[O:8]1[C:12]2([CH2:17][CH2:16][C:15](=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 59733754N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Commercially available 2-methyl-propane-2-sulfinic acid amide is reacted with commercially available 1,4-dioxa-spiro[4.5]decan-8-one in the presence of a coupling agent such as Ti(OEt)4 or CuSO4, in an organic solvent such as dichloromethane, THF or dioxane, at a temperature in the range of about 25° C. to about 80° C., to yield 2-methyl-propane-2-sulfinic acid (1,4-dioxa-spiro[4.5]dec-8-ylidene)-amide. 2-Methyl-propane-2-sulfinic acid (1,4-dioxa-spiro[4.5]dec-8-ylidene)-amide is treated with an organometalic agent such as R1MgBr or R1Li, in an organic solvent such as ether, THF or dioxane, at a temperature in the range of about ˜78° C. to about 25° C., to yield the corresponding sulfonamide (XXVI).

Sources & evidence

ORD record
ord-bbe0f74c7ef14dcd918594b0936f80f6
Source dataset
uspto-grants-2012_12
Patent number
US08324186B2

Reaction notes

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