Sodium Hydroxide → HCID 89713970, compound

HRID 1483021Notes

Reaction equation

HRID 1483021 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[N:7]\[S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 707414-BromobenzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 89713970HCID 89713970, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add (R)-2-methylpropane-2-sulfinamide (40.5 g, 0.33 mol) portion-wise to a solution of 4-bromobenzaldehyde (65.57 g, 0.35 mol) in toluene (283 mL). Stir the mixture at ambient temperature for 15 minutes and then add sodium hydroxide (1.34 g, 0.33 mol). Stir the suspension at ambient temperature for 12 hours. Add sodium sulphate (16 g) and Celite® (16 g) and stir the suspension for 15 minutes. Filter and concentrate the filtrate under reduced pressure. Purify by silica gel chromatography eluting with hexane/EtOAc (100% to 70% hexane) to afford the title compound as a white solid (85.5 g, 88% yield). MS (m/z): 288 (M+1).

Workup

  1. stirringStir the suspension at ambient temperature for 12 hours
  2. filtrationFilter
  3. concentrationconcentrate the filtrate under reduced pressure
  4. customPurify by silica gel chromatography
  5. washeluting with hexane/EtOAc (100% to 70% hexane)

Sources & evidence

ORD record
ord-6311c230e3c5429393374aa7ff84161e
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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