Dimethylformamide → HCID 19081242, compound

HRID 963497Notes

Reaction equation

HRID 963497 reaction equation
[C:1]([C:4]1[C:5]([CH2:10]O)=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CN(C)C=O.S(Cl)([Cl:19])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(Cl)(Cl)Cl>[C:1]([C:4]1[C:5]([CH2:10][Cl:19])=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 19081152HCID 19081152, compound

Product 1

HCID 19081242HCID 19081242, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-acetyl-2-hydroxymethylpyridine(0.2 g) in dichloromethane(10 ml) was treated with catalytic amount of N,N-dimethylformamide. To the mixture was added dropwise a solution of thionyl chloride (1 ml) in dichloromethane (2 ml) at ca. 5° C. in an ice-water bath. The mixture was stirred for 1 hour under the same condition, and then at room temperature for 40 minutes. To the mixture was added carefully dropwise saturated sodium carbonate aqueous solution under stirring in an ice-water bath. The mixture was taken up with chloroform and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 3-acetyl-2-chloromethylpyridine (0.11 g) as a black oil.

Workup

  1. waitat room temperature for 40 minutes
  2. stirringunder stirring in an ice-water bath
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57dd439f1c214fc5b2d564d09808c723
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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