Water → HCID 12901252, compound

HRID 1589207Notes

Reaction equation

HRID 1589207 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[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:16])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[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 173842Ahr 6293HCID 5360545Sodium

Product 1

HCID 12901252HCID 12901252, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fourteen g of 2-amino-3-(4-chlorobenzoyl)benzene acetic acid, sodium salt.H2O was dissolved in 150 ml of dimethylformamide and then treated with 30 g of ethyl iodide. The resulting solution was stirred at room temperature for 2.5 hours. The solution was then added to water and the mixture was extracted several times with benzene. The benzene layer obtained was washed with dilute base and water, dried over sodium sulfate and stripped to leave an oil which crystallized on trituration with pet. ether. Recrystallization from ethyl alcohol gave 11.6 g of the titled compound as yellow flakes, m.p. 101°-102° C.

Workup

  1. extractionthe mixture was extracted several times with benzene
  2. customThe benzene layer obtained
  3. washwas washed
  4. additionwith dilute base and water
  5. dry with materialdried over sodium sulfate
  6. customto leave an oil which
  7. customcrystallized on trituration with pet. ether
  8. customRecrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-87062308bf374ce2830aa886862b8b8b
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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