1-Propylpyrrolidine-2,4-dione → HCID 19895507, compound

HRID 1110366Notes

Reaction equation

HRID 1110366 reaction equation
C([CH:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:12][CH2:13][CH3:14])[C:7]1=[O:15])(OCC)=O.[CH2:16]([N:19]1[CH2:23][C:22](=O)[CH2:21][C:20]1=[O:25])[CH2:17][CH3:18].[NH2:26][C:27]1[C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][S:29][C:28]=1[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].O.C1(C)C=CC=CC=1>C(#N)C.C1(C)C=CC=CC=1>[CH2:12]([N:8]1[CH2:9][C:10](=[O:11])[CH2:6][C:7]1=[O:15])[CH2:13][CH3:14].[CH2:16]([N:19]1[CH2:23][C:22]([NH:26][C:27]2[C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][S:29][C:28]=2[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:21][C:20]1=[O:25])[CH2:17][CH3:18]

Participants

8

Reactant 4

HCID 135603831-Propylpyrrolidine-2,4-dioneHCID 14074904HCID 14074904, compoundHCID 19895520HCID 19895520, compoundHCID 22272177Toluene water

Product 2

HCID 135603831-Propylpyrrolidine-2,4-dioneHCID 19895507HCID 19895507, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

Freshly prepared 1-propyl-2,4-dioxopyrrolidine was prepared as described in Example 1e from 3-carboethoxy-1-propyl-2,4-dioxopyrrolidine (3.55 g) in acetonitrile (100 ml). The 1-propyl-2,4-dioxopyrrolidine was mixed with methyl 3-amino-2-pentylthiophene-4-carboxylate (2.70 g) in toluene (65 ml). The mixture was refluxed for 2 hours with removal of the water/toluene azeotrope using a Dean-Stark trap. After distilling off the excess toluene, the residue was taken up in ethyl acetate, washed sequentially with saturated aqueous Na2CO3 and brine, then dried (Na2SO4) and concentrated. Chromatographic purification over silica gel afforded the title product (3.92 g, 94%) as a yellow oil; tlc, Rf =0.12, silica gel, ethyl acetate:hexane (1:1).

Workup

  1. distillationAfter distilling off the excess toluene
  2. washwashed sequentially with saturated aqueous Na2CO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customChromatographic purification over silica gel

Sources & evidence

ORD record
ord-adfe987bd3554d20b65115943ffda4e8
Source dataset
uspto-grants-1990_12
Patent number
US04975435

Reaction notes

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