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

HRID 1609302Notes

Reaction equation

HRID 1609302 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]3[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=3)[S:7][CH:8]=2)[CH2:3][CH2:2]1.[C:18]1(=[O:29])[O:24][C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]2[CH2:19]1>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:29])[CH2:19][C:20]4[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=4[C:22]([OH:24])=[O:23])[CH:14]=[CH:15][CH:16]=3)[S:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12801Homophthalic anhydrideHCID 15136080(E)-3-[2-[4-(cyclopropyl)-2-thiazolyl]ethenyl]benzeneamine

Product 1

HCID 20084358(E)-2-[2-[3-[2-[4-(cyclopropyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acidYield 88.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.0 g of (E)-3-[2-[4-(cyclopropyl)-2-thiazolyl]ethenyl]benzeneamine, 3.35 g of homophthalic anhydride, and 100 ml of toluene was heated to reflux for 0.5 hr. After cooling, the solids that formed were collected by filtration and this material was triturated with ethyl ether to yield 7.4 g of (E)-2-[2-[3-[2-[4-(cyclopropyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid. Recrystallization from acetonitrile yielded 5.1 g of material; m.p. 200°-201° C.

Workup

  1. temperatureto reflux for 0.5 hr
  2. temperatureAfter cooling
  3. customthe solids that formed
  4. filtrationwere collected by filtration
  5. customthis material was triturated with ethyl ether

Sources & evidence

ORD record
ord-cf5e1c51026b46dab62c9603648e1cc7
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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