Methanol → HCID 66868610, compound

HRID 1519058Notes

Reaction equation

HRID 1519058 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[C:11](=[O:12])[C:10]([CH:13](O)[C:14]([F:17])([F:16])[F:15])=[CH:9][NH:8][C:7]=1[CH3:19].CO.[Cl:22]CCl>C(#N)C>[Cl:22][CH:13]([C:10]1[C:11](=[O:12])[C:6]([OH:5])=[C:7]([CH3:19])[NH:8][CH:9]=1)[C:14]([F:17])([F:16])[F:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 25018649HCID 25018649, compound

Product 1

HCID 66868610HCID 66868610, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thionyl chloride (2.5 mL, 33.7 mmol) was added to a suspension of 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (1.50 g, 6.7 mmol) in acetonitrile (33 mL) at room temperature. The resulting mixture was stirred for 30 min as a clear solution resulted. The progress of the reaction was monitored by TLC (methanol:dichloromethane, 1:10, v:v), which indicated consumption of the starting material. The reaction mixture was evaporated to dryness to give crude 5-(1-chloro-2,2,2-trifluoro-ethyl)-3-hydroxy-2-methyl-1H-pyridin-4-one as a solid.

Workup

  1. customresulted
  2. customconsumption of the starting material
  3. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-4558c03fd6054e408cfa2e302f22e113
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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