Hydrochloric Acid → 2-(Thiophen-2-ylmethyl)isoindoline-1,3-dione

HRID 492226Notes

Reaction equation

HRID 492226 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][NH2:18].Cl>C1(C)C=CC=CC=1>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][N:18]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 34005(2-Thienylmethyl)amine

Product 1

HCID 33541542-(Thiophen-2-ylmethyl)isoindoline-1,3-dioneYield 91.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of commercially available phthalic anhydride 1 (500 mg, 3.38 mmol) in toluene (30 mL) at room temperature was added thiophene-2-methylamine (463 mg, 4.1 mmol) and the resulting reaction mixture was allowed to stir at reflux for 2 hours. The reaction mixture was poured onto 1N HCl and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to provide 750 mg of 11 as a pale yellow solid (812 mg theoretical, 91% yield).

Workup

  1. customthe resulting reaction mixture
  2. temperatureat reflux for 2 hours
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a36048006574a6eba98c44417a996f7
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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