Hydrochloric Acid → HCID 18424281, compound

HRID 1606155Notes

Reaction equation

HRID 1606155 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-].[CH3:15][N:16]1[C:20]([CH2:21][C:22]#[N:23])=[CH:19][CH:18]=[CH:17]1.Cl>C(Cl)CCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:17]2[N:16]([CH3:15])[C:20]([CH2:21][C:22]#[N:23])=[CH:19][CH:18]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424281HCID 18424281, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

An acylating solution is prepared by the slow addition of 278 g. (1.58 moles) of p-chlorobenzoyl chloride to 210 g. (1.58 moles) of aluminum chloride in 750 ml. of ethylene chloride. The resulting solution is added to a solution of 190 g. (1.58 moles) of N-methylpyrrole-2-acetonitrile in 750 ml. of ethylene chloride. The temperature is maintained at 20°-22°C. during the addition; and the solution is further stirred at room temperature for one hour. The solution is then heated rapidly to 74°-76°C. at which point there is a vigorous evolution of hydrogen chloride gas. This temperature is maintained about 5 minutes and the solution is cooled rapidly and poured into ice water. The product is extracted with methylene chloride and washed with water. The organic solution is then shaken with an excess of an aqueous solution of N,N-dimethylaminopropylamine followed by dilute hydrochloric acid in order to remove any excess p-chlorobenzoyl chloride. After a final wash with brine, the solution is dried over anhydrous magnesium sulfate. Distillation of the solvent leaves a residue which crystallizes. Recrystallization from methyl alcohol yields the product, 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetonitrile, m.p. 120°-124°C. After two additional recrystallizations from methanol, the m.p. is 127°-131°C.

Workup

  1. customAn acylating solution is prepared by the slow addition of 278 g
  2. additionThe resulting solution is added to a solution of 190 g
  3. temperatureThe temperature is maintained at 20°-22°C. during the addition
  4. temperatureThe solution is then heated rapidly to 74°-76°C. at which point there
  5. temperatureThis temperature is maintained about 5 minutes
  6. temperaturethe solution is cooled rapidly
  7. extractionThe product is extracted with methylene chloride
  8. washwashed with water
  9. stirringThe organic solution is then shaken with an excess of an aqueous solution of N,N-dimethylaminopropylamine
  10. customto remove any excess p-chlorobenzoyl chloride
  11. washAfter a final wash with brine
  12. dry with materialthe solution is dried over anhydrous magnesium sulfate
  13. distillationDistillation of the solvent
  14. customleaves a residue which
  15. customcrystallizes
  16. customRecrystallization from methyl alcohol

Sources & evidence

ORD record
ord-baa26eaf12e94c35b8d11519aa3ea235
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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