Sulfuryl chloride → HCID 18407243, compound

HRID 1016558Notes

Reaction equation

HRID 1016558 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[CH2:11][CH2:10]3)[CH:2]=1.S(Cl)([Cl:20])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:20][CH:11]1[CH2:10][C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:8]=2)[C:12]1=[O:16]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 18407230HCID 18407230, compound

Product 1

HCID 18407243HCID 18407243, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3.22 g of 5-pyridin-3-yl-1-indanone are dissolved in 160 ml of dichloromethane and, at 0° C., a solution of 1.34 ml of sulfuryl chloride in 40 ml of dichloromethane is added dropwise over the course of 15 minutes. After stirring at 0° C. for 30 minutes and then at room temperature for 60 minutes, 50 ml of a saturated sodium bicarbonate solution are slowly added. The organic phase is separated off, washed with water, dried over magnesium sulfate, concentrated in vacuo and purified by chromatography on silica gel with 50/1 dichloromethane/methanol. 2-Chloro-5-pyridin-3-yl-1 indanone with a melting point of 103-105° C. is obtained (in addition to 2,2-dichloro-5-pyridin-3-yl-1-indanone with a melting point of 109° C.).

Workup

  1. waitat room temperature for 60 minutes
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography on silica gel with 50/1 dichloromethane/methanol

Sources & evidence

ORD record
ord-91afe8497bab4341ba3701ff8750f2c3
Source dataset
uspto-grants-2002_11
Patent number
US06476059B1

Reaction notes

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