Thionyl Chloride → HCID 23226983, compound

HRID 1956182Notes

Reaction equation

HRID 1956182 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[C:11]([S:16][CH3:17])=[N:12][CH:13]=[N:14][CH:15]=1)O.S(Cl)([Cl:20])=O>ClCCl>[Cl:20][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[C:10]1[C:11]([S:16][CH3:17])=[N:12][CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23227016HCID 23227016, compound

Product 1

HCID 23226983HCID 23226983, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 9.5 g (38 mmol) of (2-fluorophenyl) (4-methylthio-5-pyrimidinyl)methanol in 50 mL of dichloromethane was added slowly with stirring 10 g (84 mmol) of thionyl chloride. The resulting solution was stirred 1 hr. and then was concentrated by evaporation under reduced pressure. The resulting amber oil was diluted with 5 mL of dichloromethane and then 100 mL of hexane. The light tan solid that formed was collected by filtration and dried under reduced pressure to obtain 10.1 g (99 percent of theory) of the title compound in crude form melting at 144°-145° C.

Workup

  1. concentrationand then was concentrated by evaporation under reduced pressure
  2. additionThe resulting amber oil was diluted with 5 mL of dichloromethane
  3. customThe light tan solid that formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c78cc081ac974731851807a676b90da8
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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