4-(Trifluoromethyl)benzaldehyde → (R)-N-(4-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide

HRID 445359Notes

Reaction equation

HRID 445359 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[F:8][C:9]([F:19])([F:18])[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1>C(Cl)Cl>[F:8][C:9]([F:18])([F:19])[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[N:7][S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 68498575(R)-N-(4-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-methylpropane-2-sulfinamide (31.6 g, 260 mmol), 4-(trifluoromethyl)-benzaldehyde (22.7 g, 130 mmol) and cupric sulfate (83.2 g, 521 mmol) were added to 300 mL DCM and the mixture was stirred for 36 h. The mixture was filtered through a pad of celite and the filtrate was evaporated and purified via silica plug filtration. (R)—N-(4-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide was obtained as a white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated
  3. filtrationpurified via silica plug filtration

Sources & evidence

ORD record
ord-831372cf1646424bbaf41d789a1a005b
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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