2,5-Bis(trifluoromethyl)benzaldehyde → (NE)-N-[[2,5-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 12602

Reaction equation

HRID 12602 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:4]=1[CH:5]=O.[C:17]([S:21]([NH2:23])=[O:22])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl.O.[O-]S([O-])(=O)=O.[Cu+2]>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:4]=1/[CH:5]=[N:23]/[S:21]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:22]

Participants

6

Reactant 2

HCID 27378072,5-Bis(trifluoromethyl)benzaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 57987489(NE)-N-[[2,5-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamideYield 91%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,5-bis trifluoromethyl benzaldehyde (21.5 g, 88.8 mmol), tert butyl sulfinamide (16.1 g, 133 mmol) and anhydrous CuSO4 (16.5 g, 103 mmol) in DCM (94 ml) was stirred at room temperature for 16 hours and at reflux for 3 days. The fine suspension was diluted with water and extracted with DCM. The extracts were washed with water, dried (MgSO4) and evaporated in vacuo to an off white solid which was purified by chromatography (silica, 4-10% EtOAc/isohexane) to give the desired N-{(1E)-[2,5-bis(trifluoromethyl)phenyl]methylene}-2-methylpropane-2-sulfinamide as a white crystalline solid (14.8 g, 91%); 1H NMR δ (ppm)(CDCl3): 8.98 (1 H, d, J=1.8 Hz), 8.46 (1 H, s), 7.92-7.85 (2 H, m), 1.29 (9 H, s); m/z (ES+) 346 (MH+).

Workup

  1. temperatureat reflux for 3 days
  2. extractionextracted with DCM
  3. washThe extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo to an off white solid which
  6. customwas purified by chromatography (silica, 4-10% EtOAc/isohexane)

Sources & evidence

ORD record
ord-bcbee99499544c32b5f10b72d55104b4
Source dataset
uspto-grants-2010_06
Patent number
US07728022B2

Linked notes

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