Thionyl Chloride → HCID 58370342, compound

HRID 1894983Notes

Reaction equation

HRID 1894983 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11]O)[C:6]=1[CH3:13])(=[O:4])=[O:3].S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:11][C:7]1[C:6]([CH3:13])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58370338HCID 58370338, compound

Product 1

HCID 58370342HCID 58370342, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
62.5 °C

Procedure

To a mixture of (4-Methanesulfonyl-3-methyl-pyridin-2-yl)-methanol (13 g) and chloroform (130 ml) was added thionylchloride (7.5 ml) at 25-30° C. The reaction mixture was then heated to 60-65° C. and maintained at the same temperature for about 30 min. The solvent was distilled off completely under vacuum at 50-55° C. Ethylacetate (52 ml) was added to the crude followed by cooling to 0-10° C. and maintaining the same temperature for about 2 hrs. The compound is then filtered and washed the solid with ethylacetate (10 ml). The compound at 50-55° C. to obtain 12.2 gm of the title compound characterized by 1HNMR data (300 MHz): δ 2.75 (s, 3H), 3.38 (s, 3H), 4.95 (s, 2H), 7.82 (d, 1H), 8.70 (d, 1H) and mass [M]+: 220.06.

Workup

  1. temperaturemaintained at the same temperature for about 30 min
  2. distillationThe solvent was distilled off completely under vacuum at 50-55° C
  3. additionEthylacetate (52 ml) was added to the crude
  4. temperatureby cooling to 0-10° C.
  5. temperaturemaintaining the same temperature for about 2 hrs
  6. filtrationThe compound is then filtered
  7. washwashed the solid with ethylacetate (10 ml)

Sources & evidence

ORD record
ord-cd80eaeb0ece416784c8c04d05a291e0
Source dataset
uspto-grants-2013_08
Patent number
US08513427B2

Reaction notes

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