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

HRID 1894671Notes

Reaction equation

HRID 1894671 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 isopropoxide (114 mL, 0.38 mol) at r.t. After 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 precipitate obtained 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, J 7.54, 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. waitwas continued for 17 h at r.t
  2. customthe precipitate obtained
  3. filtrationwas filtered
  4. washwashed with DCM
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-660e7ab3062d4d2d8509c56b438c4967
Source dataset
uspto-grants-2013_08
Patent number
US08513284B2

Reaction notes

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