HCID 12436397, compound → (E)-5-acetoxy-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid

HRID 327581Notes

Reaction equation

HRID 327581 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(O[C:23]1[CH:34]=[C:27]2[CH2:28][C:29]([O:31][C:32](=[O:33])[C:26]2=[CH:25][CH:24]=1)=[O:30])(=O)C>C1(C)C=CC=CC=1>[C:29]([O:31][C:24]1[CH:23]=[CH:34][C:27]([CH2:28][C:29]([NH:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12](/[CH:11]=[CH:10]/[C:7]3[S:8][CH:9]=[C:5]([CH:1]4[CH2:4][CH2:3][CH2:2]4)[N:6]=3)[CH:13]=2)=[O:30])=[C:26]([CH:25]=1)[C:32]([OH:31])=[O:33])(=[O:30])[CH3:28]

Participants

4

Reactant 2

HCID 12436397HCID 12436397, compoundHCID 15136086(E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine

Product 1

HCID 20084344(E)-5-acetoxy-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acidYield 148.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture composed of 0.58 g of (E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine, 0.48 g of 5-acetoxyhomophthalic anhydride and 50 ml of toluene was heated on a steam bath for 0.5 hr. The mixture was cooled and the solids that formed were isolated by filtration to yield 0.77 g of (E)-5-acetoxy-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid; m.p. 176°-179° C. after trituration with hot acetonitrile.

Workup

  1. temperaturewas heated on a steam bath for 0.5 hr
  2. temperatureThe mixture was cooled
  3. customthe solids that formed
  4. customwere isolated by filtration

Sources & evidence

ORD record
ord-0a06943cd11547c48555d45bd6d5995b
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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