Triethylamine → 1-allyl-N-(3-ethylphenyl)-1H-pyrrole-2-carboxamide

HRID 1352873Notes

Reaction equation

HRID 1352873 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([OH:11])=O)[CH:2]=[CH2:3].[CH2:12]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])[CH3:13].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.S([O-])(O)(=O)=O.[K+]>ClCCl>[CH2:1]([N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[C:14]([CH2:12][CH3:13])[CH:15]=1)=[O:11])[CH:2]=[CH2:3]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 114753-EthylanilineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 516920Potassium bisulfateHCID 450820081-(prop-2-en-1-yl)-1H-pyrrole-2-carboxylic acid

Product 1

HCID 229286871-allyl-N-(3-ethylphenyl)-1H-pyrrole-2-carboxamideYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-allyl-1H-pyrrole-2-caboxylic acid (270 mg, 1.79 mmol), m-ethylaniline (0.43 g, 2.48 mmol), BOP-Cl (500 mg, 1.96 mmol) and triethylamine (210 mg, 2.08 mmol) in dichloromethane (3 ml) was stirred for 2 hours at room temperature. To the reaction mixture was added an aqueous 5% potassium hydrogensulfate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=5:1→3:1) to give the subject compound (229 mg, 50%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=5:1→3:1)

Sources & evidence

ORD record
ord-66308b2ef61e4ea69cc21d7056b756be
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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