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

HRID 1609301

Reaction equation

HRID 1609301 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-cd4b02a587ce485f921286c70636a79e
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Linked notes

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