Dimethylformamide → 5-(1-Benzoyloxymethyl)-3-chloro-2-methylthiopyridine

HRID 2302237Notes

Reaction equation

HRID 2302237 reaction equation
[Cl:1][C:2]1[C:3]([S:11][CH3:12])=[N:4][CH:5]=[C:6]([CH:8]([OH:10])C)[CH:7]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CN(C=[O:27])C>O>[C:15]([O:10][CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([S:11][CH3:12])=[N:4][CH:5]=1)(=[O:27])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 184358003-Chloro-5-(1-hydroxyethyl)-2-methylthiopyridine

Product 1

HCID 184605395-(1-Benzoyloxymethyl)-3-chloro-2-methylthiopyridineYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Chloro-5-(1-hydroxyethyl)-2-methylthiopyridine (21.9 g, 0.108 mol) was dissolved with stirring in anhydrous DMF (250 mL) and 60% sodium hydride (5 g, 0.125 mol) added in portions. The mixture was stirred at room temperature for 30 minutes and benzyl bromide (17.6 g, 0.103 mol) added dropwise. The mixture was then stirred at room temperature for four hours, diluted with water (400 mL) and extracted three times with ethyl acetate (100 mL). The combined organic extracts were washed twice with water (200 mL) and saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulphate, and evaporated to dryness. Purification of the residue by chromatography over silica (0-5% ethyl acetate:hexane) gave the desired product (25.0 g, 79%) as a pale yellow oil.

Workup

  1. stirringThe mixture was then stirred at room temperature for four hours
  2. extractionextracted three times with ethyl acetate (100 mL)
  3. washThe combined organic extracts were washed twice with water (200 mL) and saturated sodium chloride solution (100 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. customPurification of the residue by chromatography over silica (0-5% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-b3fd9e405cec4ec08f881ce16dec9ad2
Source dataset
uspto-grants-2002_08
Patent number
US06432951B1

Reaction notes

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