2-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone → 2-[(Bis-formyl)amino]-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone

HRID 841039Notes

Reaction equation

HRID 841039 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[N:7]([CH3:19])[CH:6]=1)=[O:4].[CH:20]([N-:22][CH:23]=[O:24])=[O:21].[Na+]>C(#N)C>[CH:20]([N:22]([CH:23]=[O:24])[CH2:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[N:7]([CH3:19])[CH:6]=1)=[O:4])=[O:21]

Participants

4

Reactant 2

HCID 105419432-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanoneHCID 10877056Sodium Diformylamide2×

Product 1

HCID 212566812-[(Bis-formyl)amino]-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanoneYield 54.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 10 g (0.034 mole) of 2-chloro-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone and 3.8 g (0.041 mole) sodium diformylamide in 80 mL acetonitrile was heated under reflux overnight under argon. An additional 2.0 g portion of sodium diformylamide was added and reflux was continued for 1.5 hrs. After evaporation of the solvent in vacuo the residue was passed through a flash column (silica gel, 3:1 hexane:acetone the 2:1 hexane:acetone) to give 6.18 g of a solid. mp 279-282° C. 260° C. decomp. mass spectrum (Cl—CH4) m/z=333 (M+1). NMR 300 MHz (CDCl3) d 9.0 (s, 2 H); 7.8 (d, 2 H); 7.55 (s, 1 H); 7.45 (d, 2 H); 7.1 (s, 1H); 4.85 (s, 2 H); 4.1 (s, 3 H).

Workup

  1. temperatureunder reflux overnight under argon
  2. temperaturereflux
  3. customAfter evaporation of the solvent in vacuo the residue

Sources & evidence

ORD record
ord-05270257c7684f2c9a0e147508b2b611
Source dataset
uspto-grants-2002_04
Patent number
US06369228B2

Reaction notes

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