Water → HCID 20329875, compound

HRID 2058077Notes

Reaction equation

HRID 2058077 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.Br[C:21]([CH3:28])([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]=[CH:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][C:21]([CH3:28])([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:18]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 7851113230-50-0

Product 1

HCID 20329875HCID 20329875, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(a) 2.38 g of 50% sodium hydride is suspended in 75 ml of anhydrous dimethylformamide, and 7.5 g of 4-[N-(4-methoxyphenyl)formimidoyl]phenol is added in four portions to the suspension at room temperature with stirring. Subsequently, 9.65 g of ethyl 2-bromo-2-methylpropionate is added dropwise to the resulting mixture at 20° to 25° C. over a period of about 40 minutes. The mixture is stirred at room temperature for 1 hour and then at 50° to 55° C. for 2 hours. The reaction mixture is poured into cold water, extracted with ether, and the extract is washed with 5% aqueous solution of sodium hydroxide until disappearance of the color of the aqueous layer, then washed with water and dried. After drying, the ether is distilled off to give 7.5 g of ethyl 2-[4-{N-(4-methoxyphenyl)formimidoyl}phenoxy]-2-methylpropionate in the form of an oil.

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. extractionextracted with ether
  3. washthe extract is washed with 5% aqueous solution of sodium hydroxide until disappearance of the color of the aqueous layer
  4. washwashed with water
  5. customdried
  6. customAfter drying
  7. distillationthe ether is distilled off

Sources & evidence

ORD record
ord-67e7d9571b094164a165504eaf98b36f
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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