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

HRID 1609312Notes

Reaction equation

HRID 1609312 reaction equation
[CH:1]1([C:6]2[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]3[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=3)[S:9][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]1(=[O:31])[O:26][C:24](=[O:25])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]2[CH2:21]1.C1(C)C=CC=CC=1>O1CCCC1>[CH:1]1([C:6]2[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]3[CH:14]=[C:15]([NH:19][C:20](=[O:31])[CH2:21][C:22]4[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=4[C:24]([OH:26])=[O:25])[CH:16]=[CH:17][CH:18]=3)[S:9][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 12801Homophthalic anhydrideHCID 15136082(E)-3-[2-[4-(cyclopentyl)-2-thiazolyl]ethenyl]benzeneamine

Product 1

HCID 20084332(E)-2-[2-[3-[2-[4-(cyclopentyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.7 g of (E)-3-[2-[4-(cyclopentyl)-2-thiazolyl]ethenyl]benzeneamine, 1.78 g of homophthalic anhydride and 40 ml of toluene was heated to reflux for 0.5 hr. Cooling and filtration yielded 3.75 g of (E)-2-[2-[3-[2-[4-(cyclopentyl)-2-thiazolyl]ethenyl]phenyl=amino]-2-oxoethyl]benzoic acid; m.p. 209°-210° C. from tetrahydrofuran.

Workup

  1. temperatureto reflux for 0.5 hr
  2. temperatureCooling
  3. filtrationfiltration
  4. customyielded 3.75 g of (E)-2-[2-[3-[2-[4-(cyclopentyl)-2-thiazolyl]ethenyl]phenyl=amino]-2-oxoethyl]benzoic acid

Sources & evidence

ORD record
ord-59011f1a219f4c28a2e3b240c25d012f
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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