4-Chlorobenzoyl chloride → HCID 18424299, compound

HRID 1282345Notes

Reaction equation

HRID 1282345 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:15]([N:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][C:28]#[N:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCCl>[CH2:15]([N:22]1[C:26]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:25][CH:24]=[C:23]1[CH2:27][C:28]#[N:29])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18424242HCID 18424242, compound

Product 1

HCID 18424299HCID 18424299, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 8.43 ml. (0.0663 mole) of p-chlorobenzoyl chloride and 8.8 g. (0.0663 mole) of aluminum chloride in 100 ml. of 1,2-dichloroethane is added to a solution of 13.0 g. (0.0663 mole) of 1-benzylpyrrole-2-acetonitrile in 50 ml. of 1,2-dichloroethane at 5° C. over a 5 minute period. The mixture is stirred for 15 minutes, and then heated quickly to reflux for 3 minutes. The reaction mixture is poured into ice-hydrochloric acid and then filtered. The aqueous layer is separated and washed with chloroform. The combined organic solutions are washed successively with N,N-dimethylaminopropylamine solution, dilute hydrochloric acid, and brine and then dried over anhydrous magnesium sulfate. The solvent is evaporated and the oily residue dissolved in benzene-methylcyclohexane and seeded with crystals of 1-benzyl-4-(p-chlorobenzoyl)-pyrrole-2-acetonitrile. After crystallization of the latter substance is complete, the mother liquor is filtered and evaporated and the residue crystallized from methanol. The crystals thus obtained are recrystallized from methanol to give 1-benzyl-5-(p-chlorobenzoyl)-pyrrole-2-acetonitrile as a yellow solid, m.p. 104-106° C.

Workup

  1. temperatureheated quickly
  2. temperatureto reflux for 3 minutes
  3. filtrationfiltered
  4. customThe aqueous layer is separated
  5. washwashed with chloroform
  6. washThe combined organic solutions are washed successively with N,N-dimethylaminopropylamine solution, dilute hydrochloric acid, and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent is evaporated
  9. dissolutionthe oily residue dissolved in benzene-methylcyclohexane
  10. customAfter crystallization of the latter substance
  11. filtrationthe mother liquor is filtered
  12. customevaporated
  13. customthe residue crystallized from methanol
  14. customThe crystals thus obtained
  15. customare recrystallized from methanol

Sources & evidence

ORD record
ord-e609755ff31c46d58cff9c4b052ecbde
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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