Tert-Butanesulfinamide → HCID 59278446, compound

HRID 1698275Notes

Reaction equation

HRID 1698275 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([S:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>ClC(Cl)C.ClCCl.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[N:16]/[S:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 59278446HCID 59278446, compound

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-pyridine-3-carbaldehyde (1.0 g, 5.38 mmol), 2-methylpropane-2-sulfinamide (715 mg, 5.90 mmol) and titanium (IV) isopropoxide (2.5 mL, 8.53 mmol) in dichloroethane (10 mL) was warmed at 110° C. in the microwave for 15 minutes. The reaction was monitored by TLC (ethyl acetate-hexanes 2:8). The mixture was diluted with dichloromethane (100 mL) and water (5 mL) was added. The mixture was stirred for 10 minutes and then dried over magnesium sulfate. The crude material was purified by silica gel chromatography eluting with a gradient of 0-20% ethyl acetate in hexanes to afford 2-methyl-propane-2-sulfinic acid 1-(6-bromo-pyridin-3-yl)-meth-(E)-ylideneamide

Workup

  1. additionwas added
  2. dry with materialdried over magnesium sulfate
  3. customThe crude material was purified by silica gel chromatography
  4. washeluting with a gradient of 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-090e563dd745468285f9269eca55b114
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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