Hydrochloric Acid → HCID 23469005, compound

HRID 128238Notes

Reaction equation

HRID 128238 reaction equation
[I-].[C:2]1([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[CH2:13][N+:14]([CH3:17])([CH3:16])C)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1C=CN=[CH:19]1.[ClH:23]>C(O)C.CCOCC>[ClH:23].[C:2]1([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[CH2:13][N:14]2[CH:16]=[CH:19][N:18]=[CH:17]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 23468995HCID 23468995, compound

Product 1

HCID 23469005HCID 23469005, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of [1-phenyl-pyrrol-2-yl]methyl trimethylammonium iodide (J.A.C.S., 73, 4921, (1951) (3.42 g) and imidazole (0.68 g) in ethanol (70 ml) was heated under reflux for 7 hours. The solution was evaporated and the residue was chromatographed on silica gel. Elution with chloroform gave an oil which was dissolved in ether. Addition of an excess of ethereal hydrogen chloride gave a precipitate which was filtered off and crystallised from methanol/ethyl acetate to give 1-phenyl-2-(imidazol-1-ylmethyl) pyrrole hydrochloride (0.65 g), m.p. 140°-141°.

Workup

  1. temperatureunder reflux for 7 hours
  2. customThe solution was evaporated
  3. customthe residue was chromatographed on silica gel
  4. washElution with chloroform
  5. customgave an oil which
  6. customgave a precipitate which
  7. filtrationwas filtered off
  8. customcrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-8659d4dced824854a96d135435bdd79c
Source dataset
uspto-grants-1981_03
Patent number
US04259345

Reaction notes

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