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

HRID 370918Notes

Reaction equation

HRID 370918 reaction equation
[CH3:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.ClS(O)(=O)=O.[CH3:17][N:18]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]1[CH2:24][C:25]([O:27][CH3:28])=[O:26].[Cl:29]([OH:33])(=[O:32])(=[O:31])=[O:30]>CCOCC>[Cl:29]([OH:33])(=[O:32])(=[O:31])=[O:30].[CH3:17][N:18]1[C:22]([C:3](=[N:2][CH3:1])[C:4]2[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=2)=[C:21]([CH3:23])[CH:20]=[C:19]1[CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 24638Chlorosulfonic acidHCID 12410496N-Methyl 4-Methylbenzimidoyl ChlorideHCID 13221886Methyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 18598660Methyl 1,4-Dimethyl-5-[(methylimino)(4-methylphenyl)methyl]-1H-pyrrole-2-acetate PerchlorateYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-Methyl 4-methylbenzimidoyl chloride (5.44 g, 32.5 mmole) was placed in a dry 50 ml round bottom flask and treated with alcohol free chloroform (13 ml) and chlorosulfonic acid (0.38 g, 3.2 mmole). The reaction was placed under a nitrogen atmosphere and stirred at room temperature. Methyl 1,4-dimethyl-1H-pyrrole-2-acetate (5.39 g, 32.3 mmole) was added and the reaction was stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate. The phases were separated, and the organic phase was extracted with saturated aqueous sodium bicarbonate and water, then dried over sodium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting red-brown viscous liquid was dissolved in absolute ethanol and treated with 70% perchloric acid (5.1 g, 35.5 mmole). The solution was cooled and treated with ether to induce crystallization. The solid was isolated by filtration, washed with cold ethanol, and air dried to yield 7.86 g (61%) of the title compound, m.p. 119°-124° C. (dec).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  3. customThe phases were separated
  4. extractionthe organic phase was extracted with saturated aqueous sodium bicarbonate and water
  5. dry with materialdried over sodium sulfate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe resulting red-brown viscous liquid was dissolved in absolute ethanol
  9. temperatureThe solution was cooled
  10. customcrystallization
  11. customThe solid was isolated by filtration
  12. washwashed with cold ethanol, and air
  13. customdried

Sources & evidence

ORD record
ord-d01244befd9a4f77a91437bf42281382
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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