Water → (2,4-Dichlorophenyl)(1,3,5-trimethyl-1H-pyrrol-2-yl)-methanone

HRID 841032Notes

Reaction equation

HRID 841032 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH2:12]C(O)=O)=[CH:8][C:7]=1[CH3:16])=[O:5].O>C(O)(=O)CC>[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH3:12])=[CH:8][C:7]=1[CH3:16])=[O:5]

Participants

4

Reactant 2

HCID 962WaterHCID 155177175-(2,4-Dichlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid

Product 1

HCID 15517718(2,4-Dichlorophenyl)(1,3,5-trimethyl-1H-pyrrol-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

A solution of 62.69 g (0.18 mole) 5-(2,4-dichlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid (4) in 550 mL of propionic acid was heated under reflux overnight then poured into water. The solution was extracted three times with diethyl ether. The ether solution was washed successively with NaHCO3, water and brine, and dried (MgSO4). Evaporation of the solvent in vacuo gave a tan solid which was recrystallized from methylcyclohexane: mp 96-98° C.; mass spectrum (Cl—CH4) m/z=282 (M+1); NMR 300 MHz (CDCl3) d 7.5 (s, 1H); 7.35-7.2 (m, 2 H); 5.8 (s, 1H ); 3.9 (s, 3 H); 2.25 (s, 3 H); 1.6 (s, 3 H). Anal Calcd for C14H13Cl2NO: C, 59.59; H, 4.64; N, 4.96. Found: C, 59.79; H, 4.39; N, 4.92.

Workup

  1. temperatureunder reflux overnight
  2. extractionThe solution was extracted three times with diethyl ether
  3. washThe ether solution was washed successively with NaHCO3, water and brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent in vacuo
  6. customgave a tan solid which
  7. customwas recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-62e9964f779e4834b51bb2d1912aa822
Source dataset
uspto-grants-2002_04
Patent number
US06369228B2

Reaction notes

Loading…