2-Methylpyridine → HCID 13185026, compound

HRID 2272880Notes

Reaction equation

HRID 2272880 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].Cl[S:9]([OH:12])(=[O:11])=[O:10]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[S:9](=[O:12])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 79752-Methylpyridine2×HCID 24638Chlorosulfonic acid

Product 1

HCID 13185026HCID 13185026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 ml 3-neck RBF equipped with a magnetic stir bar, thermocouple probe, addition funnel, nitrogen inlet adapter, and a rubber septum, was charged dichloromethane (anh) (25 ml) and 2-picoline (11.88 ml, 120 mmol). This picoline solution was chilled in an ice/NaCl bath to −3.5° C. Then a solution of chlorosulfonic acid (3.82 ml, 57.1 mmol) in dichloromethane (anh) (25 ml) was added over 50 minutes, with the temperature being maintained below 5° C. The resulting pale yellow solution was stirred for 1 h at room temperature before being added to the sulfation reaction at room temperature as described in this Example, step 2.

Workup

  1. customTo a 100 ml 3-neck RBF equipped with a magnetic stir bar
  2. additionthermocouple probe, addition funnel, nitrogen inlet adapter
  3. temperaturebeing maintained below 5° C
  4. additionbefore being added to the sulfation reaction at room temperature

Sources & evidence

ORD record
ord-a40a354104e542eeb0b381e8911d4d4f
Source dataset
uspto-grants-2015_09
Patent number
US09120796B2

Reaction notes

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