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

HRID 635813Notes

Reaction equation

HRID 635813 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, 2H); 5.8 (s, 1H); 3.9 (s, 3H); 2.25 (s, 3H); 1.6 (s, 3H). 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-69c5edf2c7494d35bd3144e9a4d454f6
Source dataset
uspto-grants-2001_02
Patent number
US06191142B1

Reaction notes

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