1-Heptyl-1H-imidazole → HCID 178443957, compound

HRID 1380355Notes

Reaction equation

HRID 1380355 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:26]([N:33]1[CH:37]=[CH:36][N:35]=[CH:34]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[CH3:25][C:22]1[CH:21]=[CH:20][C:19]([S:16]([O-:18])(=[O:17])=[O:15])=[CH:24][CH:23]=1.[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][N+:35]2[CH:36]=[CH:37][N:33]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:34]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 1866691-Heptyl-1H-imidazoleHCID 538442024-Methylbenzenesulfonic acid 4-(4-acetylaminophenyl)butyl ester

Product 1

HCID 178443957HCID 178443957, compound

Procedure

Heat a mixture of 6.23 g (0.017 mole) 4-methylbenzenesulfonic acid 4-(4-acetylaminophenyl)butyl ester and 2.9 g (0.017 mole) 1-heptyl-1H-imidazole to 80° C., for 5 hours, following the reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 90:10). At the completion of the reaction, triturate the cooled resultant material with petroleum ether. Recrystallize the material from 25 ml hot methyl ethyl ketone with hot filtration, chill and seed to obtain the title compound.

Workup

  1. temperatureHeat
  2. customthe reaction by thin-layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 90:10)
  3. customAt the completion of the reaction
  4. customtriturate the
  5. temperaturecooled resultant material with petroleum ether
  6. customRecrystallize the material from 25 ml hot methyl ethyl ketone
  7. filtrationwith hot filtration
  8. temperaturechill

Sources & evidence

ORD record
ord-46b82c06d62d4b9483e4f339ef40c8ee
Source dataset
uspto-grants-1986_04
Patent number
US04581370

Reaction notes

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