Sulfuric acid magnesium salt (1:1) → (NE,S)-N-[3-(3,4-dichlorophenyl)propylidene]-2-methylpropane-2-sulfinamide

HRID 1771099Notes

Reaction equation

HRID 1771099 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl.CC1C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10]/[CH:11]=[N:19]/[S@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 234995723-(3,4-Dichlorophenyl)propanal

Product 1

HCID 89477639(NE,S)-N-[3-(3,4-dichlorophenyl)propylidene]-2-methylpropane-2-sulfinamideYield 80.2%

Reagents, catalysts & solvents 2

HCID 161440Pyridine 4-methylbenzene-1-sulfonateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 16A (1.0 g, 4.9 mmol) in CH2Cl2 (5 mL) was added (S)-2-methylpropane-2-sulfinamide (0.72 g, 5.9 mmol) followed by the addition of pyridine 4-methylbenzenesulfonate (0.062 g, 0.25 mmol) and MgSO4 (2.96 g, 24.6 mmol). The reaction mixture was stirred at rt for 18 h, and then filtered through a celite pad. The filtrate was concentrated under reduced pressure and the residue was purified by ISCO chromatography (EtOAc/Hexanes 0-30% over 15 min, column 80 g, flow rate 85 mL/min) to give Intermediate 16B (1.20 g, 3.93 mmol, 80.0% yield) as a white solid. HPLC/MS (Method D) RT=1.13 min, [M+1]+ 306.0.

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by ISCO chromatography (EtOAc/Hexanes 0-30% over 15 min, column 80 g, flow rate 85 mL/min)

Sources & evidence

ORD record
ord-47c012b89fcf407c860e2a0688d3c48e
Source dataset
uspto-grants-2016_02
Patent number
US09249096B2

Reaction notes

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