Water → ethyl 2-[4-{N-(4-chlorophenyl)formimidoyl}phenoxy]-2-methylpropionate

HRID 2058078Notes

Reaction equation

HRID 2058078 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.Br[C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].O>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 868344Alpha-(4-chlorophenylimino)-P-cresol

Product 1

HCID 14871452ethyl 2-[4-{N-(4-chlorophenyl)formimidoyl}phenoxy]-2-methylpropionateYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(a) 0.312 g of 50% sodium hydride is suspended in 10 ml of anhydrous dimethylformamide, and 1.16 g of 4-[N-(4-chlorophenyl)formimidoyl]phenol is added to the suspension at 20° to 25° C. with stirring. Subsequently over a period of 15 minutes, 1.27 g of ethyl 2-bromo-2-methylpropionate is added dropwise to the resulting mixture at the same temperature with stirring. The mixture is stirred at the same temperature for 30 minutes, then at 50° to 55° C. for 2 hours and thereafter at 80° C. for 3 hours. The reaction mixture is poured into cold water, extracted with ether, and the extract is washed with 5% aqueous solution of sodium hydroxide and then with water. After drying, the solvent is distilled off to give 1.5 g of ethyl 2-[4-{N-(4-chlorophenyl)formimidoyl}phenoxy]-2-methylpropionate.

Workup

  1. stirringwith stirring
  2. stirringThe mixture is stirred at the same temperature for 30 minutes
  3. waitat 50° to 55° C. for 2 hours
  4. waitat 80° C. for 3 hours
  5. extractionextracted with ether
  6. washthe extract is washed with 5% aqueous solution of sodium hydroxide
  7. customAfter drying
  8. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-9c50817927d447b5add43f3ca75ba12d
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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