Pyridine → HCID 19763675, compound

HRID 248431Notes

Reaction equation

HRID 248431 reaction equation
[CH3:1][N:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](=[O:12])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6]1.N1C=CC=CC=1.S(Cl)([Cl:29])=O.C(OCC)(=O)C>C(Cl)Cl>[CH3:1][N:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](=[O:12])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([CH2:10][Cl:29])=[CH:6]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 19763703HCID 19763703, compound

Product 1

HCID 19763675HCID 19763675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methyl-N-phenethyl-2-[3-hydroxymethylpyrrol-1-yl]acetamide and pyridine in methylene chloride is added dropwise 2 molar equivalents of thionyl chloride. The resulting mixture is stirred at room tenperature for 18 hours and ethyl acetate is added. The solution is washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue obtained is purified by a silica gel flash column to give N-methyl-N-phenethyl-2-[3-chloromethylpyrrol-l-yl]acetamide which is used directly in the next step.

Workup

  1. washThe solution is washed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue obtained
  5. customis purified by a silica gel flash column

Sources & evidence

ORD record
ord-e92f60b2b6c04803b83a493103e59097
Source dataset
uspto-grants-1993_05
Patent number
US05210208

Reaction notes

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