Triethylamine → 3-Cyano-4-methyl-2-(2-oxopyrrolidin-1-yl)-5-phenylpyrrole

HRID 565446Notes

Reaction equation

HRID 565446 reaction equation
[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4]=1[NH2:15])#[N:2].C(N(CC)CC)C.Cl[CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>C1COCC1>[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:5][C:4]=1[N:15]1[CH2:24][CH2:25][CH2:26][C:27]1=[O:28])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 101765402-Amino-3-cyano-4-methyl-5-phenylpyrrole

Product 1

HCID 158712963-Cyano-4-methyl-2-(2-oxopyrrolidin-1-yl)-5-phenylpyrroleYield 22.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 3-cyano-4-methyl-2-amino-5-phenylpyrrole (4.9 g) in THF (80 ml) was added triethylamine (2.5 g) and while the mixture was stirred at −50° C., 4-chlorobutyryl chloride (3.5 g) was added. This reaction mixture was then stirred at room temperature for 1.5 hours, after which the insoluble matter was filtered off. The filtrate was diluted with ethyl acetate and the organic layer was washed with water and saturated aqueous solution of sodium hydrogen carbonate, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from benzene/n-hexane. The crystals were suspended in ethanol (40 ml), and potassium tert-butoxide (1.32 g) was added thereto. The mixture was stirred at room temperature overnight and the resulting crystals were collected by filtration, washed with water, and air-dried. The crude crystals thus obtained were recrystallized from ethanol to provide the title compound as light-yellow needles (1.5 g). m.p. 140-141° C.

Workup

  1. stirringThis reaction mixture was then stirred at room temperature for 1.5 hours
  2. filtrationafter which the insoluble matter was filtered off
  3. additionThe filtrate was diluted with ethyl acetate
  4. washthe organic layer was washed with water and saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from benzene/n-hexane
  8. additionpotassium tert-butoxide (1.32 g) was added
  9. stirringThe mixture was stirred at room temperature overnight
  10. filtrationthe resulting crystals were collected by filtration
  11. washwashed with water
  12. customair-dried
  13. customThe crude crystals thus obtained
  14. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-3daa98b5b61343f3943785d783fd775a
Source dataset
uspto-grants-2001_01
Patent number
US06172102B2

Reaction notes

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