Thionyl Chloride → HCID 22175642, compound

HRID 1797498Notes

Reaction equation

HRID 1797498 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([CH2:17]O)=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S(Cl)([Cl:27])=O>N1C=CC=CC=1.O1CCCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([CH2:17][Cl:27])=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 22175389HCID 22175389, compound

Product 1

HCID 22175642HCID 22175642, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-3-hydroxymethyl-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (8.7 g, 22.5 mmol) and pyridine (5 drops) in tetrahydrofuran (30 mL) and toluene (30 mL) was added thionyl chloride (3.4 mL, 47.3 mmol). The obtained mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated, poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 6-bromo-3-chloromethyl-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (8.2 g, 90%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into water
  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-59bee84513a44c04b6014858471f6aea
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…