Pyrrole → (4-chlorophenyl)(1H-pyrrol-2-yl)methanone

HRID 1414737Notes

Reaction equation

HRID 1414737 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6](N(C)C)=[O:7])=[CH:4][CH:3]=1.O(Cl)Cl.[NH:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.O.O.O.C([O-])(=O)C.[Na+]>ClCCCl.ClC(Cl)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:17]2[NH:16][CH:20]=[CH:19][CH:18]=2)=[O:7])=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 8027PyrroleHCID 24646Chlorine monoxideHCID 841804-Chloro-N,N-dimethylbenzamideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 640241(4-chlorophenyl)(1H-pyrrol-2-yl)methanone

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 183 g (1 mole) of p-chloro-N,N-dimethylbenzamide and 153g (1 mole) of phophorous oxychloride in 300 ml of 1,2-dichloroethane is heated under reflux for 30 minutes, after which a solution of 67g (1 mole) of pyrrole in 300 ml of dichloroethane is added drop-wise. It is cooled and a solution of 408g (3 moles) of sodium acetate trihydrate in 1600 ml of water is added dropwise for 45 minutes, after which the mixture is again heated under reflux for 30 minutes. The resulting mixture is poured onto ice, the organic layer is separated, and the aqueous layer is washed with chloroform. The combined organic solutions are washed with sodium bicarbonate and brine and dried over magnesium sulfate. Evaporation of the solvent in vacuo gives a dark oil, which is distilled in vacuo through a heated Vigreaux column to give a white solid; mp 106°-9° C. It is recrystallized from cyclohexane to give 2-p-chlorobenzoylpyrrole as white needles; m.p. 110°-113° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureIt is cooled
  4. temperatureafter which the mixture is again heated
  5. temperatureunder reflux for 30 minutes
  6. additionThe resulting mixture is poured onto ice
  7. customthe organic layer is separated
  8. washthe aqueous layer is washed with chloroform
  9. washThe combined organic solutions are washed with sodium bicarbonate and brine
  10. dry with materialdried over magnesium sulfate
  11. customEvaporation of the solvent in vacuo
  12. customgives a dark oil, which
  13. distillationis distilled in vacuo through a heated Vigreaux column
  14. customto give a white solid
  15. customIt is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-414c975692b64857858b3c4e3b124a93
Source dataset
uspto-grants-1977_01
Patent number
US04002643

Reaction notes

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