Perchloric Acid → Methyl 1,4-Dimethyl-5-[(methylimino)phenylmethyl]-1H-pyrrole-2-acetate Perchlorate

HRID 370931

Reaction equation

HRID 370931 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH3:13][N:14]=[C:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl:23]([OH:27])(=[O:26])(=[O:25])=[O:24]>Cl.C(Cl)(Cl)Cl>[Cl:23]([OH:27])(=[O:26])(=[O:25])=[O:24].[CH3:1][N:2]1[C:6]([C:15](=[N:14][CH3:13])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 576277N-Methylbenzimidoyl chlorideHCID 13221886Methyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 20275546Methyl 1,4-Dimethyl-5-[(methylimino)phenylmethyl]-1H-pyrrole-2-acetate PerchlorateYield 62.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6212ChloroformSolvent

Procedure

Methyl 1,4-dimethyl-1H-pyrrole-2-acetate (1.66 g, 10 mmole) was placed in a 25 ml round bottom flask and treated with alcohol free chloroform (2 ml) and N-methyl benzimidoyl chloride (1.78 g, 12 mmole). The solution was treated with several drops of ethereal hydrogen chloride--mild exotherm. The reaction was protected with a calcium chloride drying tube and stirred at room temperature for about four hours. The reaction was diluted with chloroform, quenched into saturated sodium bicarbonate, washed with brine, dried over sodium sulfate, filtered and concentrated. The viscous residue was dissolved in absolute ethanol (6 ml) and treated with 70% perchloric acid (1.42 g, 10 mmole). The resulting crystalline solid was isolated by filtration and washed with ethanol/ether (1 to 3 by volume) and air dried to yield 2.39 g (62%) of the title compound as a bright yellow solid, m.p. 149°-150° C.

Workup

  1. customThe reaction was protected with a calcium chloride drying tube
  2. customquenched into saturated sodium bicarbonate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe viscous residue was dissolved in absolute ethanol (6 ml)
  8. customThe resulting crystalline solid was isolated by filtration
  9. washwashed with ethanol/ether (1 to 3 by volume) and air
  10. customdried

Sources & evidence

ORD record
ord-7cbb866646d74c24aaeb22e4caf4a4eb
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Linked notes

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