Ammonia → 4-(2,3-Dichlorophenyl)-1H-pyrrole-3-carboxamide

HRID 274738Notes

Reaction equation

HRID 274738 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:14]([OH:16])=O)=[CH:11][NH:12][CH:13]=1.C([N:19](CC)CC)C.S(Cl)(Cl)=O.CN(C)C=O.N>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:14]([NH2:19])=[O:16])=[CH:11][NH:12][CH:13]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6228DimethylformamideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 152390934-(2,3-Dichlorophenyl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 200936224-(2,3-Dichlorophenyl)-1H-pyrrole-3-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2,3-dichlorophenyl)pyrrole-3-carboxylic acid (2.43 g, 9.5 mmol) and triethylamine (7 mL, 50 mmol) in tetrahydrofuran is stirred for 15 minutes at room temperature and concentrated in vacuo to obtain a residue. A mixture of the residue, thionyl chloride (2.77 mL, 38 mmol) and N,N-dimethylformamide (0.73 mL, 9.5 mmol) is stirred overnight at room temperature and concentrated in vacuo to obtain a yellow oil. The oil is added to a concentrated ammonia solution and stirred for 1 hour. This mixture is filtered to give a solid. The solid is washed with water, dried and chromatographed using silica gel and a 4:1 hexanes/ethyl acetate mixture to obtain the title product as a white solid (1.6 g, mp 185°-190° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain a residue
  3. stirringis stirred overnight at room temperature
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow oil
  6. stirringstirred for 1 hour
  7. filtrationThis mixture is filtered
  8. customto give a solid
  9. washThe solid is washed with water
  10. customdried
  11. customchromatographed

Sources & evidence

ORD record
ord-5e2f0bfe6a79442597767eb817a04aba
Source dataset
uspto-grants-1995_02
Patent number
US05389669

Reaction notes

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