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

HRID 1729178Notes

Reaction equation

HRID 1729178 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].C(O)(=O)CC>O>[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 1032Propionic AcidHCID 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 962WaterSolvent

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-37b6512c92f24ef39ba78c1fe248d86d
Source dataset
uspto-grants-1994_07
Patent number
US05332736

Reaction notes

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