4-Chlorobenzoyl chloride → HCID 18424299, compound

HRID 1585606Notes

Reaction equation

HRID 1585606 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. (0.067 mole) of p-chlorobenzoyl chloride and 8.8 g. (0.067 mole) of aluminum chloride in 100 ml. of 1,2-dichloroethane is added to a solution of 13.0 g. (0.067 mole) of 1-benzylpyrrole-2acetonitrile in 50 ml. of 1,2-dichloroethane at 5° C. over a 5 minute period. The reaction mixture is stirred for 15 minutes and then heated quickly to reflux for 3 minutes. The mixture is poured into ice-hydrochloric acid and then filtered. The aqueous layer is separated and washed with chloroform. The combined organic fractions are washed successively with N,N-dimetylaminopropylamine solution, dilute hydrochloric acid and brine and then dried over anhydrous magnesium sulfate. The solvent is evaporated to yield an oily residue from which the desired compound is isolated by column chromatography on neutral alumina with a 50--50 mixture of benzene ether as the eluting solvent. Evaporation of the elute affords 1-benzyl-5-(p-chlorobenzoyl)-pyrrole-2-acetonitrile as a yellow solid which is recrystallized from methanol, m.p. 106-108° 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 fractions are washed successively with N,N-dimetylaminopropylamine solution, dilute hydrochloric acid and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent is evaporated

Sources & evidence

ORD record
ord-902fef77036c4fb9b13ba48828ee1e83
Source dataset
uspto-grants-1999_08
Patent number
US05939417

Reaction notes

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