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

HRID 370917Notes

Reaction equation

HRID 370917 reaction equation
[CH3:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.ClS(O)(=O)=O.[CH3:18][N:19]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]1[CH2:25][C:26]([O:28][CH3:29])=[O:27].[Cl:30]([OH:34])(=[O:33])(=[O:32])=[O:31]>C(O)C.CCOCC>[Cl:30]([OH:34])(=[O:33])(=[O:32])=[O:31].[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3](=[N:2][CH3:1])[C:23]2[N:19]([CH3:18])[C:20]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:21][C:22]=2[CH3:24])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 24247Perchloric AcidHCID 24638Chlorosulfonic acidHCID 12410495N-Methyl 4-Methoxybenzimidoyl ChlorideHCID 13221886Methyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 20275540Methyl 5-[(4-methoxyphenyl)(methylimino)methyl]-1,4-dimethyl-1H-pyrrole-2-acetate PerchlorateYield 70.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

N-Methyl 4-methoxybenzimidoyl chloride (6.67 g, 36.4 mmole) was placed in a dry 50 ml round bottom flask and treated with alcohol free chloroform (13 ml) and chlorosulfonic acid (0.42 g, 3.6 mmole). The reaction was blanketed with nitrogen and stirred while methyl 1,4-dimethyl-1H-pyrrole-2-acetate (6.03 g., 36.1 mmole) was added dropwise over a period of about five minutes. The reaction was stirred overnight, then heated at 40° C. for two hours. The reaction was quenched with saturated aqueous sodium bicarbonate. The phases were separated, and the organic phase was washed with saturated aqueous sodium bicarbonate and water, then dried over sodium sulfate. The chloroform was removed under reduced pressure to yield a red viscous liquid. The crude product was dissolved in absolute ethanol and treated with 70% perchloric acid (5.7 g, 40 mmole). The solution was cooled and treated with ether to induce crystallization. The yellow solid was isolated by filtration and washed with cold ethanol to yield 10.5 g (64%) of the title compound, m.p. 123°-129° C. (dec).

Workup

  1. additionwas added dropwise over a period of about five minutes
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  3. customThe phases were separated
  4. washthe organic phase was washed with saturated aqueous sodium bicarbonate and water
  5. dry with materialdried over sodium sulfate
  6. customThe chloroform was removed under reduced pressure
  7. customto yield a red viscous liquid
  8. temperatureThe solution was cooled
  9. customcrystallization
  10. customThe yellow solid was isolated by filtration
  11. washwashed with cold ethanol

Sources & evidence

ORD record
ord-a3dad859bb824726a3147dfe0704e216
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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