Water → HCID 53974068, compound

HRID 261513Notes

Reaction equation

HRID 261513 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:15])[C:12]([OH:14])=[O:13].[C:21]([O-])(=O)[CH3:22].[Na+].C(Br)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:15])[C:12]([O:14][CH2:21][CH3:22])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 517045Sodium AcetateHCID 15646809HCID 15646809, compound

Product 1

HCID 53974068HCID 53974068, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.2 g of 2-(2,6-dichloroanilino)-phenylglyoxylic acid in 30 ml of dimethylformamide were added 3.3 g of anhydrous sodium acetate and then dropwise added 3 ml of ethyl bromide under ice-cooling. The mixture was stirred at room temperature for 10 hours. Thereafter, the reaction mixture was poured into 300 ml of water and the whole mixture was extracted with benzene. The benzene extract was washed with water, dried over anhydrous sodium sulfate and then concentrated. The residue was subjected to column chromatography with silica gel (Wacogel C 200), using etherhexane (1:2) as a developing solvent, to give 5.3 g of ethyl 2-(2,6-dichloroanilino)phenylglyoxylate as yellow crystals. m.p. 84°-85° C. Yield: 78% of theoretical amount

Workup

  1. extractionthe whole mixture was extracted with benzene
  2. extractionThe benzene extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-43e6308868f44bd4a66f9157e6c8a247
Source dataset
uspto-grants-1979_08
Patent number
US04166128

Reaction notes

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