Toluene → (E)-5-methoxy-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid

HRID 1609339Notes

Reaction equation

HRID 1609339 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.CO[C:21]1[CH:32]=[C:25]2[CH2:26][C:27]([O:29][C:30](=[O:31])[C:24]2=[CH:23][CH:22]=1)=[O:28].C1(C)C=CC=CC=1.[O:40]1CCC[CH2:41]1>>[CH3:41][O:40][C:22]1[CH:21]=[CH:32][C:25]([CH2:26][C:27]([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:28])=[C:24]([CH:23]=1)[C:30]([OH:29])=[O:31]

Participants

5

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 110196745-Methoxyhomophthalic anhydrideHCID 15136086(E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine

Product 1

HCID 20084319(E)-5-methoxy-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid

Procedure

A solution of 0.4 g of (E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine, 0.4 g of 5-methoxyhomophthalic anhydride, 50 ml of toluene and 10 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 ethanol to yield (E)-5-methoxy-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid, m.p. 190°-191° C.

Workup

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

Sources & evidence

ORD record
ord-bc6466854cf84088bfb72420786eb254
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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