Phthalic Anhydride → 2-[[(2-Thienylmethyl)amino]carbonyl]benzoic acid

HRID 2113731Notes

Reaction equation

HRID 2113731 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[C:8]1(=[O:18])[O:13][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12>C(Cl)(Cl)Cl>[S:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[CH2:2][NH:1][C:8](=[O:18])[C:9]1[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 34005(2-Thienylmethyl)amine

Product 1

HCID 178101612-[[(2-Thienylmethyl)amino]carbonyl]benzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-aminomethyl-thiophene (2.1 ml, 20.5 mmol) in CHCl3 (25 ml) is treated with phthalic anhydride (3.0 g, 20.5 mmol) at r.t. for 5 min, then at reflux for 20 min, whereupon a white powder precipitated out. This powder is collected by filtration and dried in vacuo to give N-thiophen-2-ylmethyl-phthalamic acid (4.42 g, 83%) as white crystals. An aliquot of this phthalamic acid (2.13 g, 8.12 mmol) is dissolved in MeOH (12 ml), treated with H2SO4 (440 μl, 8.25 mmol) and heated to reflux for 1.5 h, whereupon a white powder precipitated out. This powder is collected by filtration and dried in vacuo to give 1.38 g (70%) of the title phthalimide as white crystals: 1H NMR (DMSO-d6) δ7.92-7.82 (m., 4H), 7.42 (dd, J=5.1, 1.2 Hz, 1H), 7.08 (dd, J=4.0, 0.8 Hz, 1H), 6.95 (dd, J=5.1, 3.5 Hz, 1H), 4.92 (s, 2H).

Workup

  1. temperatureat reflux for 20 min, whereupon a white powder
  2. customprecipitated out
  3. filtrationThis powder is collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c9d12c86adfd4a6f95cf79e0ded4cad2
Source dataset
uspto-grants-2008_10
Patent number
US07432286B1

Reaction notes

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