Dimethyl Sulfoxide → HCID 53250899, compound

HRID 2170004Notes

Reaction equation

HRID 2170004 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:5]=[CH:4][CH:3]=1.[CH3:17][S:18](C)=O.C[S-].[Na+].CCCCCCC>C(OCC)(=O)C>[CH3:17][S:18][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8900HeptaneHCID 4378561Sodium methanethiolateHCID 53250569HCID 53250569, compound

Product 1

HCID 53250899HCID 53250899, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
90 °C

Procedure

Introduced into a microwave tube are 300 mg (1.28 mmol) of 2-[(6-chloropyridin-2-ylamino)methyl]phenol, to which 5 ml of dimethyl sulphoxide and 448 mg (6.4 mmol, 5 eq) of sodium methanethiolate are added. The reaction mixture is heated for 16 h at 90° C. The reaction medium is diluted with 50 ml of ethyl acetate and then washed with 50 ml of a saturated ammonium chloride solution then 2×50 ml of distilled water. The organic phase is dried over magnesium sulphate then filtered and concentrated to dryness. The residue is purified by chromatography over 40 g of silica with, as eluent, heptane/ethyl acetate (7/3). The product obtained is put back into solution in ethyl acetate, heptane is added until the solution becomes cloudy, it is then cooled to 0° C. and filtered. 2-[(6-Methylsulphanylpyridin-2-ylamino)methyl]phenol is obtained in the form of a white solid.

Workup

  1. additionIntroduced into a microwave tube
  2. washwashed with 50 ml of a saturated ammonium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationthen filtered
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by chromatography over 40 g of silica with, as eluent
  7. customThe product obtained
  8. temperatureis then cooled to 0° C.
  9. filtrationfiltered

Sources & evidence

ORD record
ord-ae1b263ebf5b4cf99422ed9244e0a022
Source dataset
uspto-grants-2015_06
Patent number
US09050266B2

Reaction notes

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