Water → (NE,R)-N-[(2,8-dichloroquinolin-3-yl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1850807Notes

Reaction equation

HRID 1850807 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]([S@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:11](/[CH:12]=[N:21]/[S@@:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 149171252,8-Dichloro-quinoline-3-carbaldehyde

Product 1

HCID 87146894(NE,R)-N-[(2,8-dichloroquinolin-3-yl)methylidene]-2-methylpropane-2-sulfinamideYield 97.5%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,8-dichloroquinoline-3-carboxaldehyde (43.0 g, 0.19 mol) in anhydrous THF (500 mL) was added titanium(IV) isopropoxide (114 mL, 0.38 mol) at r.t. After stirring for 15 minutes, (R)-2-methyl-2-propanesulfinamide (23.0 g, 0.19 mol) was added and stirring was continued for 17 h at r.t. Water (1 L) was added to the reaction mixture and the resulting precipitate was filtered and washed with DCM. The organic layer was dried (Na2SO4) and concentrated in vacuo to give the title compound (61 g, 97%) as a pale yellow solid. δH (CDCl3) 9.11 (1H, s), 8.83 (1H, s), 7.93 (1H, dd, J7.54, 1.31 Hz), 7.88 (1H, dd, J 8.22, 1.31 Hz), 7.55 (1H, t, J 7.88 Hz), 1.33 (9H, s).

Workup

  1. stirringstirring
  2. waitwas continued for 17 h at r.t
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with DCM
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48c2ad1f93234047b5d799e136e81892
Source dataset
uspto-grants-2015_02
Patent number
US08957090B2

Reaction notes

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