3-Bromobenzaldehyde → (NZ)-N-[(3-bromophenyl)methylidene]-2-methylpropane-2-sulfonamide

HRID 1527514Notes

Reaction equation

HRID 1527514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])([CH3:13])([CH3:12])[CH3:11]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:3]=[C:4](/[CH:5]=[N:17]\[S:14]([C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:16])=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 765833-BromobenzaldehydeHCID 2757335tert-Butylsulfonamide

Product 1

HCID 88922034(NZ)-N-[(3-bromophenyl)methylidene]-2-methylpropane-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-benzaldehyde (1.27 mL, 10.8 mmol) in THF (50 mL) were added titanium(IV) ethoxide (0.786 mL, 21.6 mmol) and tert-butylsulfonamide (1.31 g, 10.8 mmol), and stirring was continued for 16 h at 65° C. After cooling to RT, volatiles were evaporated, and the residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 3:1) to afford the title compound. MS (LC/MS): 289 [M+H]+; tR (HPLC conditions f): 2.35 min.

Workup

  1. customvolatiles were evaporated
  2. customthe residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-54fd60c3c49046aab97efb45aaa1497f
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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