Phosphorus oxychloride → HCID 86687424, compound

HRID 1473382Notes

Reaction equation

HRID 1473382 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[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:23]>ClCCCl>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:23])=[N:14][CH:13]=[C:12]2[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86687423HCID 86687423, compound

Product 1

HCID 86687424HCID 86687424, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

A vial was charged with 6-(benzylthio)-4-fluoroisoquinolin-1(2H)-one (0.083 g, 0.291 mmol) and DCE (1.454 ml). POCl3 (0.136 ml, 1.454 mmol) was added and the reaction was stirred overnight at 90° C. The reaction was quenched into ice water and extracted with ethyl acetate. 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-fluoroisoquinoline as a light yellow solid. The material was carried forward without further purification. (ESI) 304.1 (M+H)+.

Workup

  1. customThe reaction was quenched into ice water
  2. extractionextracted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6bbd2ed8c19c445ea035ca0072f31e8c
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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