3-Bromobenzaldehyde → (NE,R)-N-[(3-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1525280Notes

Reaction equation

HRID 1525280 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]([S@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)/[CH:5]=[N:16]/[S@@:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15]

Participants

6

Reactant 3

HCID 765833-BromobenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 45103201(NE,R)-N-[(3-bromophenyl)methylidene]-2-methylpropane-2-sulfinamideYield 93%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
37 °C

Procedure

3-bromobenzaldehyde, 24-a, (10 g, 53.9 mmol) in dichloromethane (300 ml) were added (R)-2-methylpropane-2-sulfinamide (7.84 g, 64.8 mmol), PPTS (1.97 g, 7.85 mmol) and anhydrous CuSO4 (25.8 g, 161 mmol) and the resulting mixture was stirred at 37° C. overnight. The mixture was then filtrated and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1) to provide the product, 24-b, (14.4 g, 93%).

Workup

  1. filtrationThe mixture was then filtrated
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-f5ed9642f18f49ae993a3d82ede5079c
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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