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

HRID 908543Notes

Reaction equation

HRID 908543 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-ff5f2a3294874eb9952f6664cbf276ae
Source dataset
uspto-grants-2011_09
Patent number
US08017628B2

Reaction notes

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