Sodium Carbonate → 2-(Chloromethyl)-3,5-dimethyl-4-nitropyridine

HRID 380729Notes

Reaction equation

HRID 380729 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([N+:14]([O-:16])=[O:15])[C:10]([CH3:17])=[CH:9][N:8]=1.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.C(#N)C>[Cl:3][CH2:6][C:7]1[C:12]([CH3:13])=[C:11]([N+:14]([O-:16])=[O:15])[C:10]([CH3:17])=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 24436Sodium SulfateHCID 4049415(3,5-Dimethyl-4-nitropyridin-2-yl)methanol

Product 1

HCID 112178962-(Chloromethyl)-3,5-dimethyl-4-nitropyridine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
12.5 °C

Procedure

8.0 ml (0.11 mole) of thionyl chloride in 20.0 ml of methylenechloride was added to a solution of 20.0 gms 2-hydroxymethyl-3,5dimethyl-4-nitropyridine, of formula-II obtained in step-(a), at temperature of 10-15° C. over a period of 1 hr. The reaction is maintained at 10-15° C. for further 30 min. Aqueous 10% solution of sodium carbonate was slowly added to the reaction mixture at 10-15° C. and pH adjusted to 8.0 to 8.5. The organic base (compound) is over anhydrous sodium sulfate and solvent was removed under vacuum to obtain crude product. (purity 85%) Pure compound is isolated by re-crystallization from acetonitrile.

Workup

  1. customof formula-II obtained in step-(a), at temperature of 10-15° C. over a period of 1 hr
  2. customwas removed under vacuum
  3. customto obtain crude product

Sources & evidence

ORD record
ord-dcdd1b239c514d568bf8d119fa91e1f4
Source dataset
uspto-grants-2001_10
Patent number
US06303787B1

Reaction notes

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