Cesium carbonate → (NE,S)-N-[(3-chloro-2,6-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1396319Notes

Reaction equation

HRID 1396319 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[CH:5]=O.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:18][C:19]([S@@:22]([NH2:24])=[O:23])([CH3:21])[CH3:20]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)/[CH:5]=[N:24]/[S@:22]([C:19]([CH3:21])([CH3:20])[CH3:18])=[O:23]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 7363383-Chloro-2,6-difluorobenzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89405973(NE,S)-N-[(3-chloro-2,6-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamideYield 100.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 3-chloro-2,6-difluorobenzaldehyde (0.615 g, 3.48 mmol) and Cs2CO3 (1.702 g, 5.23 mmol) in DCM (20 mL) was added a solution of (S)-2-methylpropane-2-sulfinamide (0.422 g, 3.48 mmol) in DCM (20 mL) dropwise for 10 min. The solution was then stirred at rt overnight. After overnight stirring, the reaction mixture was diluted with EtOAc and washed with brine (3×20 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product (0.98 g, 100%) as yellow oil. MS (ESI) m/z: 282.0 (M+H)+.

Workup

  1. stirringAfter overnight stirring
  2. washwashed with brine (3×20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7260bcafdbe3411db1b26cfd729d727e
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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