HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 12601
Notes
Print preview

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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962WaterSolvent
HCID 6344
Dichloromethane
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728022B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes