Thionyl Chloride → HCID 22176392, compound

HRID 1797459Notes

Reaction equation

HRID 1797459 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=2)[C:9](=[O:19])[N:8]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]=1[CH2:25]O)[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:29])=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][CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=2)[C:9](=[O:19])[N:8]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]=1[CH2:25][Cl:29])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 22175925HCID 22175925, compound

Product 1

HCID 22176392HCID 22176392, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-butoxy-6-ethoxy-3-hydroxymethyl-2-neopentyl-1(2H)-isoquinolinone (0.43 g, 1.2 mmol) in tetrahydrofuran (10 ml) and toluene (10 ml) was added thionyl chloride (0.18 ml, 2.4 mmol). 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-6-ethoxy-3-chloromethyl-2-neopentyl-1(2H)-isoquinolinone (0.41 g, 91.1%) 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-a630b5e6a85043a8a0e963a9d9bc2a96
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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