(E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine → Methyl 3-methoxybenzoate

HRID 1609340

Reaction equation

HRID 1609340 reaction equation
C1(C2N=C(/C=C/C3C=C(N)C=CC=3)SC=2)CCC1.[CH3:19][O:20][C:21](=[O:34])[C:22]1[CH:27]=[CH:26][C:25](CC(O)=O)=[C:24]([O:32][CH3:33])[CH:23]=1>C(Cl)Cl>[CH3:19][O:20][C:21](=[O:34])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:32][CH3:33])[CH:23]=1

Participants

4

Reactant 2

HCID 15136086(E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamineHCID 542548432-Methoxy-4-methoxycarbonyl-phenylacetic acid

Product 1

HCID 79332Methyl 3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution composed of 0.49 g of (E)-3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]benzeneamine, 0.43 g of 4-carboxymethyl-3-methoxybenzoic acid methyl ester, 0.4 g of N-ethyl-N-(dimethylaminopropyl)carbodiimide and 25 ml of methylene chloride was sealed in a flask and stored at 25° C. for 16 hr. The reaction mixture was then washed with 10 ml of water, dried (MgSO4) and the solvent removed by rotary evaporation. The residual material was purified by silica gel chromatography using ethyl acetate as the eluant to yield 0.62 g of (E)-4-[2-[3-[2-(4-cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]-3-methoxybenzoic acid methyl ester; m.p., 156°-157° C. from ethyl acetate.

Workup

  1. customwas sealed in a flask
  2. washThe reaction mixture was then washed with 10 ml of water
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed by rotary evaporation
  5. customThe residual material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-89a58424e4b14357beb858368c4086ec
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Linked notes

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