Water → HCID 86098782, compound

HRID 2359835Notes

Reaction equation

HRID 2359835 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[O:22][CH3:23])[OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.O>CS(C)=O>[Cl:1][C:2]1[C:11]([C:12]([C:14]2[C:15]([O:22][CH3:23])=[CH:16][CH:17]=[CH:18][C:19]=2[O:20][CH3:21])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 86639113HCID 86639113, compound

Product 1

HCID 86098782HCID 86098782, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

(2-Chloroquinolin-3-yl)(2,6-dimethoxyphenyl)methanol (0.5 g, 1.5 mmol) and triethylamine (0.84 mL, 6.1 mmol) were dissolved in dimethyl sulfoxide (20 mL) and mixed with a solution of sulfur trioxide-pyridine complex (0.72 g, 4.55 mol) in dimethyl sulfoxide (5 mL) under nitrogen. The batch was stirred at room temperature until the reaction was complete (TLC monitoring). After adding water, the mixture was stirred for 1 hour at room temperature. The precipitated product was filtered with suction, washed with water and dried in a vacuum drying cabinet (20 mbar, 50° C.). Yield: 0.45 g (1.37 mmol, 91%).

Workup

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. filtrationThe precipitated product was filtered with suction
  3. washwashed with water
  4. customdried in a vacuum
  5. customdrying cabinet (20 mbar, 50° C.)

Sources & evidence

ORD record
ord-fa4ab8a522734649bef0f1c0f522f973
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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