Thionyl Chloride → HCID 22175995, compound

HRID 1797465Notes

Reaction equation

HRID 1797465 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=2)[C:9](=[O:17])[N:8]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]=1[CH2:23]O)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:27])=O.C(=O)([O-])O.[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([F:16])=[CH:13][CH:14]=2)[C:9](=[O:17])[N:8]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]=1[CH2:23][Cl:27])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 22175702HCID 22175702, compound

Product 1

HCID 22175995HCID 22175995, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-butoxy-7-fluoro-3-hydroxymethyl-2-neopentyl-1(2H)-isoquinolinone (2.35g, 7 mmol) in tetrahydrofuran (10 ml) and toluene (10 ml) was added thionyl chloride (1.0 ml, 14 mmol) and the obtained mixture was refluxed under heating for 2 h. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with brine dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4-butoxy-7-fluoro-3-chloromethyl-2-neopentyl-1(2H)-isoquinolinone (2.04 g, 82.6%) as an oil.

Workup

  1. temperaturethe obtained mixture was refluxed
  2. temperatureunder heating for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e50da842afcd4e2c8193d4be90609a26
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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