Sodium Carbonate → HCID 11550077, compound

HRID 592145Notes

Reaction equation

HRID 592145 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[CH3:10].S(Cl)([Cl:13])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Cl:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([CH2:8][Cl:13])=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 11686949(6-Chloro-5-methylpyridin-3-yl)methanol

Product 1

HCID 11550077HCID 11550077, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (6-chloro-5-methylpyridin-3-yl)methanol 74-1 (1.57 g, 10 mmol) in dichloromethane (15 mL) was added dropwise thionyl chloride (3.6 mL, 50 mmol) at 0° C. slowly. The mixture was stirred for 2 hours at room temperature, diluted with dichloromethane (100 mL) and water (100 mL), neutralized with powder sodium carbonate to pH 8. The aqueous layer was further extracted with dichloromethane (50 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation to afford 2-chloro-5-(chloromethyl)-3-methylpyridine 74-2 as pale yellow solid, which was used for next step directly. MS m/z 176.1 (M+1)

Workup

  1. extractionThe aqueous layer was further extracted with dichloromethane (50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-84d5a4f8e1e94b5e9241f91a0f8b9747
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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