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

HRID 327541Notes

Reaction equation

HRID 327541 reaction equation
[CH:1]1([C:5]2[N:6]=[C:7](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)[S:8][CH: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>O1CCCC1>[CH:1]1([C:5]2[N:6]=[C:7](/[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)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 12801Homophthalic anhydrideHCID 15136086(E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine

Product 1

HCID 20084337(E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.28 g of (E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine, 0.81 g of homophthalic anhydride, 50 ml of toluene and 25 ml of tetrahydrofuran was heated to reflux for 0.5 hr. The solvents were removed by rotary evaporation and the residual materials were triturated with ethyl ether to yield 1.15 g of (E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid. Recrystallization from acetonitrile yielded 0.81 g of material; m.p. 204°-206° C. Anal. Calcd for C24H22N2O3S: C, 68.88; H, 5.30; N, 6.69. Found: C, 68.15; H, 5.21; N, 6.54.

Workup

  1. temperatureto reflux for 0.5 hr
  2. customThe solvents were removed by rotary evaporation
  3. customthe residual materials were triturated with ethyl ether

Sources & evidence

ORD record
ord-652bd0ec9cdf4f54baa559e6f91a5b48
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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