Hydrochloric Acid → HCID 18424281, compound

HRID 1275279Notes

Reaction equation

HRID 1275279 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×

Conditions

Temperature
21 °C

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

Sources & evidence

ORD record
ord-c356cc01a0064448bb9d7fd3a78d573e
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

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