4-Chlorobenzoyl chloride → HCID 18424207, compound

HRID 1282324Notes

Reaction equation

HRID 1282324 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([C:6]2[N:2]([CH3:1])[C:3]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:5]=2)=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 974691H-Pyrrole-2-acetic acid, 1-methyl-, ethyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424207HCID 18424207, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of (22.0 g. (0.131 mole) of ethyl N-methylpyrrole-2-acetate and 24.5 g. (0.14 mole) of p-chlorobenzoyl chloride in 120 ml. of carbon disulfide is added 35.0 g. (0.262 mole) of anhydrous aluminum chloride over a period of 20 minutes with intermittant cooling to keep the temperature at 25° C. The mixture is stirred for an additional 20 minutes. The carbon disulfide solvent is then decanted and discarded. The red gummy residue is washed with hexane and dilute hydrochloric acid and ice is added to the mixture. The mixture is extracted with ether. The ether solution is shaken with an aqueous solution of dimethylaminopropylamine and washed with dilute hydrochloric acid followed by brine. The solution is dried over magnesium sulfate and treated with charcoal. After removal of the charcoal, the solvent is evaporated in vacuo leaving a partially crystalline red oil as a residue. This material is extracted with three 500 ml. portions of boiling pentane. The combined pentane extracts are evaporated in vacuo, and the residue is crystallized from 60 ml. of cold methanol. The resulting solid is collected and washed with cold methanol; there is obtained about 6.3 g of a white crystalline solid, ethyl 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetate, m.p. 74-76° C. Recrystallization from methyl cyclohexane raises the melting point to 78-80° C.

Workup

  1. customat 25° C
  2. customThe carbon disulfide solvent is then decanted
  3. washThe red gummy residue is washed with hexane and dilute hydrochloric acid and ice
  4. additionis added to the mixture
  5. extractionThe mixture is extracted with ether
  6. stirringThe ether solution is shaken with an aqueous solution of dimethylaminopropylamine
  7. washwashed with dilute hydrochloric acid
  8. dry with materialThe solution is dried over magnesium sulfate
  9. additiontreated with charcoal
  10. customAfter removal of the charcoal
  11. customthe solvent is evaporated in vacuo
  12. customleaving a partially crystalline red oil as a residue
  13. extractionThis material is extracted with three 500 ml
  14. customThe combined pentane extracts are evaporated in vacuo
  15. customthe residue is crystallized from 60 ml
  16. customThe resulting solid is collected
  17. washwashed with cold methanol

Sources & evidence

ORD record
ord-43132b9bf037473fb93e4ca1f6aad65e
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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