tert-Butylsulfinamide, (R)-(+)- → (NE,R)-2-methyl-N-[[4-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamide

HRID 246013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246013
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=O)[CH:4]=1.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[C:5](/[CH:9]=[N:19]/[S@@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH:4]=1

Komponenten

5

Edukt 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 147614714-(Trifluoromethyl)pyridine-2-carbaldehyde

Produkt 1

HCID 89421022(NE,R)-2-methyl-N-[[4-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-trifluoromethyl-pyridine-2-carbaldehyde (287 mg, 1.64 mmol) and (R)-2-methylpropane-2-sulfinamide (209 mg, 1.72 mmol) in CH2Cl2 (10 mL) was added anhydrous copper (II) sulfate (576 mg, 3.61 mmol). The reaction mixture was stirred at room temperature overnight then filtered over a Buchner funnel, rinsing with CH2Cl2. The filtrate was concentrated and the residue was absorbed on SiO2 and purified by chromatography with 20% to 40% EtOAc/hexanes to give 340 mg (75%) of (R)-2-methyl-propane-2-sulfinic acid 1-(4-trifluoromethyl-pyridin-2-yl)-meth-(E)-ylideneamide as a pale yellow oil.

Aufarbeitung

  1. filtrationthen filtered over a Buchner funnel
  2. washrinsing with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customthe residue was absorbed on SiO2
  5. custompurified by chromatography with 20% to 40% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c960ddb87f50420680bd3681b19fc4a1
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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