Phenol → HCID 68183292, compound

HRID 513638Notes

Reaction equation

HRID 513638 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.P(Cl)(Cl)(Cl)(Cl)Cl.[C:23]1(O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.O>[C:23]1([O:5][S:2](=[O:4])(=[O:3])[NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 113598-AminoquinolineHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 68183292HCID 68183292, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonic acid (210 mg, 1.8 mmol) in DCM was added dropwise to solution of 8-aminoquinoline (250 mg, 1.7 mmol) and TEA (260 mg, 2.6 mmol) in DCM (5 ml) at 0° C. and the mixture was stirred for 30 min. The reaction was allowed to warm to room temperature and stirring was continued for 1 h. PCl5 (370 mg, 1.8 mmol) was added and the mixture was heated at 50° C. for 1 h. The reaction was cooled to room temperature, phenol (310 mg, 3.4 mmol) and TEA (340 mg, 3.4 mmol) were added and the reaction was stirred at room temperature overnight. Water was added and the mixture was extracted with DCM, the organic phase dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (4:1) as the eluent to give the title compound (40 mg, 8%).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. temperaturethe mixture was heated at 50° C. for 1 h
  4. temperatureThe reaction was cooled to room temperature
  5. stirringthe reaction was stirred at room temperature overnight
  6. extractionthe mixture was extracted with DCM
  7. dry with materialthe organic phase dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (4:1) as the eluent

Sources & evidence

ORD record
ord-5ca7991702bb498e8a394cfd6508f108
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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