Thionyl Chloride → HCID 53724591, compound

HRID 1579002Notes

Reaction equation

HRID 1579002 reaction equation
S(Cl)([Cl:3])=O.[O:5]([C:12]1[CH:13]=[C:14]([C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][N:20]=1)[C:15](O)=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O>[O:5]([C:12]1[CH:13]=[C:14]([C:18]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][N:20]=1)[C:15]([Cl:3])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54325693HCID 54325693, compound

Product 1

HCID 53724591HCID 53724591, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To thionyl chloride (3 ml), a mixture of 2-phenoxy-5-ethoxycarbonylethylisonicotinic acid (1.0 g) and dimethylformamide (a small amount) is added, and the resultant mixture is stirred at room temperature for 20 minutes. The reaction mixture is evaporated under reduced pressure to remove the thionyl chloride. The residue is mixed with dry benzene and evaporated again. The residue is dissolved in anhydrous ether, and the insoluble part is filtered off. The ether solution is evaporated to give 2-phenoxy-5-ethoxycarbonylethylisonicotinoyl chloride (1.05 g). IR (CHCl3): 1775, 1735 cm-1.

Workup

  1. additionis added
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customto remove the thionyl chloride
  4. additionThe residue is mixed with dry benzene
  5. customevaporated again
  6. dissolutionThe residue is dissolved in anhydrous ether
  7. filtrationthe insoluble part is filtered off
  8. customThe ether solution is evaporated

Sources & evidence

ORD record
ord-26f96f89894b4063950ee492bd5fcbba
Source dataset
uspto-grants-1976_02
Patent number
US03940403

Reaction notes

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