4-Toluenesulfonyl chloride → HCID 21107319, compound

HRID 1765550Notes

Reaction equation

HRID 1765550 reaction equation
[CH2:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][CH:2]1[OH:15])[N:11]=[CH:10][CH:9]=[CH:8]3.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:15][CH:2]2[CH2:3][O:4][C:5]3[C:6](=[C:7]4[C:12](=[CH:13][CH:14]=3)[N:11]=[CH:10][CH:9]=[CH:8]4)[CH2:1]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 21107318HCID 21107318, compound2×

Product 1

HCID 21107319HCID 21107319, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-ol (intermediate 10) (0.47 g, 2.3 mmol) and p-toluene sulfonyl chloride (0.89 g, 4.6 mmol) in anhydrous pyridine (20 mL) was stirred at room temperature for 2.5 days. It was then poured into ice-H2O and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Chromatography ((15:4:1) EtOAc-Hexane-MeOH) afforded 0.77 g (93%) of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-yl 4-methylbenzenesulfonate as an off-white solid: mp 167.5–169.5° C. MS ESI m/z 356 [M+H]+. Elemental Analysis for C19H17NO4S: Calculated: C, 64.21; H, 4.82; N, 3.94. Found: C, 63.98; H, 4.79; N, 3.84.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c6703bc34a944b59a39deafe9dc26f61
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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