Thionyl Chloride → HCID 67282158, compound

HRID 913035Notes

Reaction equation

HRID 913035 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[C:18](=[O:19])[C:17]([CH:20](O)[C:21]([F:24])([F:23])[F:22])=[CH:16][NH:15][C:14]=1[CH3:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CO.[Cl:29]CCl>C(#N)C>[ClH:3].[CH2:5]([O:12][C:13]1[C:18](=[O:19])[C:17]([CH:20]([Cl:29])[C:21]([F:24])([F:23])[F:22])=[CH:16][NH:15][C:14]=1[CH3:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 21226129Dichloromethane methanolHCID 67282369HCID 67282369, compound

Product 1

HCID 67282158HCID 67282158, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (7.5 mL, 102 mmol) was added to a suspension of 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (8.0 g, 25.5 mmol) in acetonitrile (100 mL) at room temperature. The resulting mixture was heated to 60° C. for 1 h. The progress of the reaction was monitored by TLC (methanol/dichloromethane 5/100 v/v as eluant). The reaction mixture (suspension) was evaporated to dryness to afford a solid. After stirring in acetonitrile, the title compound was collected by suction filtration (7.1 g, 75% yield). 1H NMR (DMSO-d6+D2O) δ ppm: 7.88 (s, 1H), 7.33 (m, 5H), 6.03 (q, J=7.3 Hz, 1H), 5.02 (s, 2H), 2.10 (s, 3H).

Workup

  1. customThe reaction mixture (suspension) was evaporated to dryness
  2. customto afford a solid
  3. filtrationthe title compound was collected by suction filtration (7.1 g, 75% yield)

Sources & evidence

ORD record
ord-e212a2f4b8e842939b4aeaa993111762
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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