Methanol → HCID 86672817, compound

HRID 1519064Notes

Reaction equation

HRID 1519064 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[C:11](=[O:12])[CH:10]=[C:9]([CH:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[N:8]([CH3:19])[C:7]=1[CH2:20]O.CO.[Cl:24]CCl>C(#N)C>[ClH:3].[Cl:24][CH2:20][C:7]1[N:8]([CH3:19])[C:9]([CH:13]([OH:18])[C:14]([F:17])([F:16])[F:15])=[CH:10][C:11](=[O:12])[C:6]=1[OH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 67282310HCID 67282310, compound

Product 1

HCID 86672817HCID 86672817, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thionyl chloride (0.48 mL, 6.6 mmol) was added dropwise to a suspension of 3-hydroxy-2-(hydroxymethyl)-1-methyl-6-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one (1.50 g, 5.9 mmol) in acetonitrile (45 mL). The progress of the reaction was monitored by TLC (eluant: methanol:dichloromethane, 15:100, v:v), and the starting material was consumed within 5 min. The reaction mixture was concentrated repeatedly in acetonitrile to give a solid, which was then washed with acetonitrile (15 mL×1). Thus, 2-(chloromethyl)-3-hydroxy-1-methyl-6-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one hydrochloride was obtained as a white solid (1.18 g).

Workup

  1. customthe starting material was consumed within 5 min
  2. concentrationThe reaction mixture was concentrated repeatedly in acetonitrile
  3. customto give a solid, which
  4. washwas then washed with acetonitrile (15 mL×1)

Sources & evidence

ORD record
ord-7b60e897e01d436397d418e767c80945
Source dataset
uspto-grants-2015_07
Patent number
US09073865B2

Reaction notes

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