2,5-Dichloroaniline → HCID 18940316, compound

HRID 355652Notes

Reaction equation

HRID 355652 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1[CH2:25][N:24]([C:26]([CH3:31])([CH3:30])[C:27]([OH:29])=O)[C:23](=[O:32])[C:22]=1[C:33]1[CH:37]=[CH:36][S:35][CH:34]=1.[Cl:38][C:39]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:40]=1[NH2:41].C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl.ClCCl>[Cl:38][C:39]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:40]=1[NH:41][C:27](=[O:29])[C:26]([N:24]1[CH2:25][C:21]([CH3:20])=[C:22]([C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)[C:23]1=[O:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 72622,5-DichloroanilineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 21829916HCID 21829916, compound

Product 1

HCID 18940316HCID 18940316, compoundYield 22.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Triphenylphosphine (1.3 g) was added to a suspension of 2-[4-methyl-2-oxo-3-(thiophen-3-yl)-3-pyrrolin-1-yl]isobutyric acid (1 g) in carbon tetrachloride (9 mL) and dichloromethane (9 mL), and the mixture was heated at reflux for 30 minutes at 70° C. After ice-cooling the reaction solution, 2,5-dichloroaniline (0.61 g) and then triethylamine (0.38 g) were added, and the mixture was stirred for 24 hours at room temperature. After the reaction was completed, distilling off the solvent, water was added and the resulting mixture was extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid and a saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous sodium sulfate. After distilling off ethyl acetate, the resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=20/1) to give 0.35 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. distillationdistilling off the solvent, water
  3. additionwas added
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with diluted hydrochloric acid
  6. dry with materiala saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous sodium sulfate
  7. distillationAfter distilling off ethyl acetate
  8. customthe resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-7df87e5300f8424586ffc8a405361b9a
Source dataset
uspto-grants-1998_11
Patent number
US05834401

Reaction notes

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