Thionyl Chloride → HCID 15431542, compound

HRID 357549Notes

Reaction equation

HRID 357549 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:10]=[CH:9][N:8]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 15166220HCID 15166220, compound

Product 1

HCID 15431542HCID 15431542, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

0.71 g (6 mmol) of thionyl chloride was added to a solution of 0.40 g (1.5 mmol) of 2-hydroxymethyl-3-methyl-4-(2-pyridylmethoxyethoxy)pyridine in 10 ml of chloroform under cooling with ice to obtain a mixture. This mixture was stirred at 0° C. for 2 hours. After the completion of the reaction, the mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with 50 ml of chloroform four times. The extract was dried over magnesium sulfate and filtered. The obtained filtrate was concentrated and dried in a vacuum to obtain 0.42 g of crude 2-chloromethyl-3-methyl-4-(2-pyridylmethoxyethoxy)pyridine as a semicrystal.

Workup

  1. temperatureunder cooling with ice
  2. customto obtain a mixture
  3. customAfter the completion of the reaction
  4. extractionextracted with 50 ml of chloroform four times
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe obtained filtrate was concentrated
  8. customdried in a vacuum

Sources & evidence

ORD record
ord-556251424eab45c5ad07e8e587220241
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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