Acetic Acid → HCID 86687437, compound

HRID 1473394Notes

Reaction equation

HRID 1473394 reaction equation
C(S[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:19])=[N:14][CH:13]=[C:12]2[OH:20])C1C=CC=CC=1.C(Cl)Cl.C(O)(=O)C.[S:28]([Cl:32])(Cl)(=[O:30])=[O:29]>O>[Cl:19][C:15]1[C:16]2[C:11](=[CH:10][C:9]([S:28]([Cl:32])(=[O:30])=[O:29])=[CH:18][CH:17]=2)[C:12]([OH:20])=[CH:13][N:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 86687436HCID 86687436, compound

Product 1

HCID 86687437HCID 86687437, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round-bottom flask was charged with 6-(benzylthio)-1-chloroisoquinolin-4-ol (0.280 g, 0.928 mmol), DCM (8.84 ml), acetic acid (0.221 ml), and water (0.221 ml) to give a thin suspension. The flask was cooled in an ice-bath for 10 min, then sulfuryl chloride (0.226 ml, 2.78 mmol) was added in one portion, leading to a solution. The reaction was stirred for 30 minutes, then warmed to room temperature and stirred for one hour. The reaction was concentrated and purified via column chromatography (40 g silica gel column, gradient elution 0 to 100% EtOAc:Heptane) to afford 1-chloro-4-hydroxyisoquinoline-6-sulfonyl chloride (as a light pink solid. (ESI) 280.1 (M+H)+.

Workup

  1. customto give a thin suspension
  2. temperatureThe flask was cooled in an ice-bath for 10 min
  3. stirringstirred for one hour
  4. concentrationThe reaction was concentrated
  5. custompurified via column chromatography (40 g silica gel column, gradient elution 0 to 100% EtOAc:Heptane)

Sources & evidence

ORD record
ord-556a037f27a74bf8bd973e00b6040ffc
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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