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

HRID 246013Notes

Reaction equation

HRID 246013 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c960ddb87f50420680bd3681b19fc4a1
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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