1,2-Dichloroethane → HCID 86687434, compound

HRID 1473392Notes

Reaction equation

HRID 1473392 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[NH:14][CH:13]=[C:12]2[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22]CCCl.O=P(Cl)(Cl)Cl>C(OCC)(=O)C>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:22])=[N:14][CH:13]=[C:12]2[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24813Phosphorus oxychlorideHCID 86687435HCID 86687435, compound

Product 1

HCID 86687434HCID 86687434, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A vial was charged with 6-(benzylthio)-4-methoxyisoquinolin-1(2H)-one (0.933 g, 3.14 mmol) and DCE (15.69 ml). POCl3 (0.585 ml, 6.27 mmol) was added and the reaction was stirred overnight at 90° C. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford crude 6-(benzylthio)-1-chloro-4-methoxyisoquinoline (Intermediate VVV) as a brown solid. (ESI) 316.3 (M+H)+.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-13d24a627ec141bd9374d55619eaf5b6
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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