Phosphorus oxychloride → HCID 86662548, compound

HRID 1616097Notes

Reaction equation

HRID 1616097 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][S:4][C:5]1[NH:10][C:9](=O)[CH:8]=[CH:7][N:6]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH2:3][C:2]([F:13])([F:12])[F:1])[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66776516HCID 66776516, compound

Product 1

HCID 86662548HCID 86662548, compoundYield 58.8%

Procedure

The solution of 2-(2,2,2-trifluoro-ethylsulfanyl)-3H-pyrimidin-4-one (25 g, crude) in POCl3 (250 mL) was stirred and refluxed for 5 hours. After most POCl3 was removed, the residue was dropped into ice and the pH was adjusted to 8-9, extracted with ethyl acetate, dried over MgSO4 and the crude material was purified by column chromatography on silica gel to give 4-chloro-2-(2,2,2-trifluoro-ethylsulfanyl)-pyrimidine (14.6 g, 58.8%) as an oil.

Workup

  1. temperaturerefluxed for 5 hours
  2. customAfter most POCl3 was removed
  3. additionthe residue was dropped into ice
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. customthe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1a0fc4997c604114b7a073011a67d223
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

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