Hydrochloric Acid → HCID 18424277, compound

HRID 1606137Notes

Reaction equation

HRID 1606137 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].ClC(Cl)C.[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[CH3:19][N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][C:26]#[N:27].Cl>>[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([C:24]1[N:20]([CH3:19])[C:21]([CH2:25][C:26]#[N:27])=[CH:22][CH:23]=1)=[O:13]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 63651,1-Dichloroethane2×HCID 691102-Chlorobenzoyl chlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424277HCID 18424277, compound

Procedure

To a cooled suspension of 14 g. (0.105 mole) aluminum chloride in 45 ml. dichloroethane is added dropwise, 18.5 g. (0.105 mole) o-chlorobenzoyl chloride. The resulting solution is added dropwise to a cooled (0°C.) solution of 1-methylpyrrole-2-acetonitrile in 45 ml. dichloroethane keeping the temperature at approximately 10°C. The mixture is stirred at room temperature for about twenty minutes, and then refluxed for three minutes. It is poured into ice acidified with 3N hydrochloric acid and the resulting two layers are separated. The aqueous fraction is extracted twice with chloroform. The organic fractions are combined and washed twice with N,N-dimethyl-1,3-propanediamine, once with 3N hydrochloric acid and once with saturated sodium chloride solution. The organic fraction is dried over anhydrous magnesium sulfate. The solvent is evaporated and the resulting oil is chromatographed on a column packed with neutral alumina using benzene and ether as successive solvents. The first compound-bearing fractions contain the desired product. The solvent is evaporated and the resulting oil crystallizes upon treatment with methanol. The solid product, 5-(o-chlorobenzoyl)-1-methylpyrrole-2-acetonitrile, is purified by recrystallization from benzene:cyclohexane solution, m.p. 80°-85°C.

Workup

  1. additionTo a cooled suspension of 14 g
  2. additionThe resulting solution is added dropwise to
  3. customat approximately 10°C
  4. temperaturerefluxed for three minutes
  5. additionIt is poured into ice
  6. customthe resulting two layers are separated
  7. extractionThe aqueous fraction is extracted twice with chloroform
  8. washwashed twice with N,N-dimethyl-1,3-propanediamine, once with 3N hydrochloric acid and once with saturated sodium chloride solution
  9. dry with materialThe organic fraction is dried over anhydrous magnesium sulfate
  10. customThe solvent is evaporated
  11. customthe resulting oil is chromatographed on a column
  12. customThe solvent is evaporated
  13. customthe resulting oil crystallizes upon treatment with methanol
  14. customThe solid product, 5-(o-chlorobenzoyl)-1-methylpyrrole-2-acetonitrile, is purified by recrystallization from benzene

Sources & evidence

ORD record
ord-3f9e2766722c4c40b31992e4c1e86819
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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