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

HRID 327540

Reaction equation

HRID 327540 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. Anal. Calcd for C23H20N2O3S: C, 68.30; H, 4.98; N, 6.93. Found: C, 67.92; H, 4.97; N, 6.83.

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-6eba70f5198f478a853ddef228d2eb90
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Linked notes

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