Homophthalic anhydride → 2-({3-[(E)-2-(4-Isopropyl-thiazol-2-yl)-vinyl]-phenylcarbamoyl}-methyl)-benzoic acid

HRID 327539

Reaction equation

HRID 327539 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=2)[S:7][CH:8]=1)[CH3:3].[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>[CH3:3][CH:2]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:29])[CH2:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])[CH:14]=[CH:15][CH:16]=2)[S:7][CH:8]=1)[CH3:1]

Participants

4

Reactant 2

HCID 12801Homophthalic anhydrideHCID 140511654-Isopropyl-2-(trans-3-aminostyryl) thiazole

Product 1

HCID 98442512-({3-[(E)-2-(4-Isopropyl-thiazol-2-yl)-vinyl]-phenylcarbamoyl}-methyl)-benzoic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.2 g of (E)-3-[2-[4-(1-methylethyl)-2-thiazolyl]ethenyl]benzeneamine, 0.8 g of homophthalic anhydride and 25 ml of toluene was heated to reflux for 0.5 hr. Upon cooling to room temperature, the solid reaction product was filtered and washed with ethyl ether to yield 1.7 g of (E)-2-[2-[3-[2-[4-(1-methylethyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid. Recrystallization from ethyl alcohol yielded off-white solid material; m.p. 203°-204° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 0.5 hr
  3. customthe solid reaction product
  4. filtrationwas filtered
  5. washwashed with ethyl ether

Sources & evidence

ORD record
ord-8d03b41a1581486ab8b8edb1afc61a2d
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Linked notes

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