Water → HCID 13577656, compound

HRID 1589206Notes

Reaction equation

HRID 1589206 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:16])=[CH:4][C:3]=1[CH2:17][C:18]([OH:20])=[O:19].[Na].O.[CH2:23](I)[CH3:24]>CN(C)C=O>[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:16])=[CH:4][C:3]=1[CH2:17][C:18]([O:20][CH2:23][CH3:24])=[O:19]

Participants

6

Reactant 4

HCID 962Water2×HCID 6340IodoethaneHCID 5360545SodiumHCID 12901227HCID 12901227, compound

Product 1

HCID 13577656HCID 13577656, compoundYield 4.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.12 g (0.1 mole) of 2-amino-3-benzoyl-5-chlorobenzeneacetic acid, sodium salt.1/2 H2O in 250 ml of dry dimethylformamide was treated with 44 g of ethyl iodide (0.3 mole) under nitrogen and stirred for 2 hours. The resulting solution was then added to one liter of water and extracted several times with ethyl ether. The combined ether layers were washed with water, dried over sodium sulfate, filtered and stripped to yield a solid yellow residue. This residue was recrystallized from ethyl alcohol, yielding 1.5 g of the title compound as yellow needles, m.p. 80°-82° C.

Workup

  1. extractionextracted several times with ethyl ether
  2. washThe combined ether layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customto yield a solid yellow residue
  6. customThis residue was recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-7e09a371909e438a9ee04b2cbbf3319d
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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