2,4-Bis(trifluoromethyl)benzaldehyde → (NE)-N-[[2,4-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 12601

Reaction equation

HRID 12601 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[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]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[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 27360952,4-Bis(trifluoromethyl)benzaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 178455562(NE)-N-[[2,4-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,4-bis trifluoromethyl benzaldehyde (10.0 g, 41.3 mmol), tert butyl sulfinamide (4.5 g, 37.2 mmol) and anhydrous CuSO4 (13.1 g, 82.6 mmol) in DCM (100 ml) was stirred at room temperature overnight. The fine suspension was diluted with water and extracted with DCM. The extracts were washed with water, dried (MgSO4) and evaporated in vacuo to afford the desired N-{(1E)-[2,4-bis(trifluoro methyl)phenyl]methylene}-2-methylpropane-2-sulfinamide as an off white solid (7.62 g, 53%), with no further purification. 1H NMR δ (ppm)(CDCl3): 8.99 (1 H, d, J=1.9 Hz), 8.35 (1 H, d, J=8.2 Hz), 8.02 (1 H, s), 7.92 (1 H, d, J=8.2 Hz), 1.28 (9 H, d, J=4.6 Hz); m/z (ES+) 346 (MH+).

Workup

  1. extractionextracted with DCM
  2. washThe extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d8a15633b09740b3a83773b2d22693a7
Source dataset
uspto-grants-2010_06
Patent number
US07728022B2

Linked notes

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