Bisulfite → HCID 90017778, compound

HRID 1055001Notes

Reaction equation

HRID 1055001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](SC)[C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].O[O:13][S:14]([O-:16])=O.[K+].S([O-])(O)=O.[C:22](=O)(O)[O-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:14]([CH3:22])(=[O:16])=[O:13])[C:5]([NH2:9])=[N:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 104748BisulfiteHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 90017776HCID 90017776, compound

Product 1

HCID 90017778HCID 90017778, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5-Chloro-6-methyl-3-methylsulfanyl-pyridin-2-ylamine (160 mg, 848 μmol, Eq: 1.00) and oxone (1.56 g, 2.54 mmol, Eq: 3) were combined in methanol (15 ml) to give an off-white suspension. The mixture was cooled to 0° C., and water (30 ml) was added dropwise, followed by 39% hydrogen sulfite (1.5 ml) and saturated sodium bicarbonate solution (6 ml). The mixture was stirred for 10 min and then extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to an oil. The product (88 mg, 47%) was obtained as a white solid by chromatography (SiO2, ethyl acetate/n-heptane). MS: m/z=221.2 (M+H+)

Workup

  1. customto give an off-white suspension
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-eebf58e8b2d9428f9ffe245687ffc582
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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