Dimethylformamide → HCID 54365005, compound

HRID 128470Notes

Reaction equation

HRID 128470 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N:20][OH:21])[C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1.CN(C)C=O>[O-]CC.[Na+].C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N:20][O:21][CH2:19][CH2:7][CH2:8][CH3:9])[C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]([CH3:17])([CH3:16])[C:13]([O:15][CH2:6][CH2:2][CH2:3][CH3:4])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 887713442-[4-(2-Thienyl-hydroxyiminomethyl)-phenoxy]-2-methyl propionic acid

Product 1

HCID 54365005HCID 54365005, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

2-[4-(2-Thienyl-hydroxyiminomethyl)-phenoxy]-2-methyl propionic acid (6.7 g) is dissolved in a sodium ethoxide solution in ethanol (100 ml; prepared from 1.3 g sodium), and the solution is then refluxed for 1 hour, after which dimethylformamide (75 ml) is added thereto and the ethanol is evaporated off. Butyl bromide (9 g) is added to the solution at 80° C. and the mixture is stirred for 3 hours, after which the solvent is evaporated under reduced pressure. Water and chloroform are then added to the resulting material. After stirring the mixture, the chloroform phase is decanted off and is then washed with an aqueous alkaline solution. After drying, the solvent is evaporated off and the desired ester is isolated as an oil consisting of an admixture of equivalent amounts of both stereoisomers Z/E. nd22 =1.545.

Workup

  1. temperaturethe solution is then refluxed for 1 hour
  2. customthe ethanol is evaporated off
  3. additionButyl bromide (9 g) is added to the solution at 80° C.
  4. customafter which the solvent is evaporated under reduced pressure
  5. additionWater and chloroform are then added to the resulting material
  6. stirringAfter stirring the mixture
  7. customthe chloroform phase is decanted off
  8. washis then washed with an aqueous alkaline solution
  9. customAfter drying
  10. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-6491b7c30363492a861ef2e9d81853ec
Source dataset
uspto-grants-1981_03
Patent number
US04259509

Reaction notes

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