Homophthalic anhydride → (E)-2-[2-[3-[2-(2-cyclobutyl-4-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]benzoic acid

HRID 1609335Notes

Reaction equation

HRID 1609335 reaction equation
[CH:1]1([C:5]2[S:6][CH:7]=[C:8](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:19]1(=[O:30])[O:25][C:23](=[O:24])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]2[CH2:20]1>C1(C)C=CC=CC=1>[CH:1]1([C:5]2[S:6][CH:7]=[C:8](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:30])[CH2:20][C:21]4[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=4[C:23]([OH:25])=[O:24])[CH:15]=[CH:16][CH:17]=3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12801Homophthalic anhydrideHCID 20084338(E)-3-[2-[2-Cyclobutyl-4-thiazolyl]ethenyl]phenylamine

Product 1

HCID 20084324(E)-2-[2-[3-[2-(2-cyclobutyl-4-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]benzoic acidYield 47.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.13 g of (E)-3-[2-[2-cyclobutyl-4-thiazolyl]ethenyl]phenylamine, 0.094 g of homophthalic anhydride and 10 ml of toluene was heated on a steam bath for 1 hr and then allowed to cool to room temperature. Filtration of the reaction mixture yielded 0.1 g of (E)-2-[2-[3-[2-(2-cyclobutyl-4-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]benzoic acid; m.p. 198°-199° C. from acetonitrile.

Workup

  1. temperaturewas heated on a steam bath for 1 hr
  2. filtrationFiltration of the reaction mixture

Sources & evidence

ORD record
ord-b1182c6ec9b34b529b36a5f9ba487275
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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