Water → HCID 71144039, compound

HRID 509315Notes

Reaction equation

HRID 509315 reaction equation
[CH3:1][C:2]([S@@:5](/[N:7]=[CH:8]/[C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:6])([CH3:4])[CH3:3].[Cl:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[CH:24][C:25]=1[Cl:26].[NH4+].[Cl-].O>C1COCC1.CCOC(C)=O>[Cl:19][C:20]1[CH:21]=[C:22]([C@@H:8]([C:9]2[C:14]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:12]=[CH:11][N:10]=2)[NH:7][S@:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 89310312(NE,S)-2-methyl-N-[[3-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamideHCID 178478192HCID 178478192, compound

Product 1

HCID 71144039HCID 71144039, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S,E)-2-Methyl-N-((3-(trifluoromethyl)pyridin-2-yl)methylene)propane-2-sulfinamide (0.493 g, 1.772 mmol) was dissolved in dry THF (10 mL) and cooled in an ice bath. 3,4-Dichlorophenylmagnesium bromide (Aldrich, 0.5 M solution in THF, 4.0 mL, 2.0 mmol) was added, and the reaction was stirred for 5 minutes. Saturated aqueous NH4Cl (10 mL), H2O (100 mL) and EtOAc (100 mL) were added and the phases were mixed and separated. The organic layer was dried with MgSO4 and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to EtOAc gradient) gave (S)—N—((S)-(3,4-dichloro-phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide.

Workup

  1. temperaturecooled in an ice bath
  2. additionthe phases were mixed
  3. customseparated
  4. dry with materialThe organic layer was dried with MgSO4
  5. customevaporated to dryness under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-4528fbbc36dc474a82bd46b6deb4d029
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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