Triethylamine → 3-Chloro-1-[4-(dimethylamino)benzyl]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113742Notes

Reaction equation

HRID 2113742 reaction equation
[Cl:1][C:2]1[C:3](=[O:14])O[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.Cl.[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(O)(=O)C>[Cl:1][C:2]1[C:3](=[O:14])[N:24]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([N:18]([CH3:27])[CH3:17])=[CH:20][CH:21]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 234471953-Chloro-4-phenylfuran-2,5-dione

Product 1

HCID 691480113-Chloro-1-[4-(dimethylamino)benzyl]-4-phenyl-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-chloro-4-phenylfuran-2,5-dione (0.20 mmol, 42 mg) and 4-dimethylaminobenzylamine dihydrochloride (0.20 mmol, 45 mg) in glacial acetic acid (1 mL) was added triethylamine (0.40 mmol). The mixture was heated in a microwave reactor at 120° C. for two min. After cooling, the solvent was evaporated at reduced pressure. The reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated at reduced pressure
  3. customThe reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Sources & evidence

ORD record
ord-d9a46a4d9eba4ec8b22273556ba49319
Source dataset
uspto-grants-2008_10
Patent number
US07432288B2

Reaction notes

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