Triethylamine → HCID 178419824, compound

HRID 280561Notes

Reaction equation

HRID 280561 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([NH2:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[IH:17].CS[C:20]1[NH:21][CH2:22][CH2:23][N:24]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(O)C.CCOCC>[IH:17].[NH:21]1[CH2:22][CH2:23][NH:24][C:20]1=[N:16][CH:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[CH:10]=[CH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]1=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2081635H-Dibenzo(a,d)cycloheptene, 5-amino-HCID 516892Sodium BicarbonateHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)

Product 1

HCID 178419824HCID 178419824, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1.04 grams (0.005 mole) of 5H-dibenzo[a,d]cyclohepten-5-ylamine, 1.22 grams (0.005 mole) of 2-methylmercapto-4,5-dihydroimidazole hydroiodide, and 1.5 milliliters of triethylamine were mixed together in 20 milliliters of ethanol and heated at reflux temperature for 16 hours. Thereafter most of the ethanol was evaporated, some n-butanol added and the resulting mixture heated under reflux for 15 hours. At the end of this period, the solvent was removed under reduced pressure, and residue obtained to which was added first, aqueous sodium bicarbonate, then ether and the resulting mixture stirred and decanted to recover the non-dissolving solid as residue. The solid was stirred overnight with ether, filtered and crystallized from ethanol. It was purified by chromatographing on a silica gel column employing 6 percent methanol in chloroform as eluant to obtain the desired N-(2-imidazolidinylidene)-5H-dibenzo[a,d]cyclohepten-5-amine hydroiodide product. Elemental analyses were as follows:

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 16 hours
  3. customThereafter most of the ethanol was evaporated
  4. additionsome n-butanol added
  5. temperaturethe resulting mixture heated
  6. temperatureunder reflux for 15 hours
  7. customAt the end of this period, the solvent was removed under reduced pressure, and residue
  8. customobtained to which
  9. additionwas added first
  10. customdecanted
  11. customto recover the non-dissolving solid as residue
  12. filtrationfiltered
  13. customcrystallized from ethanol
  14. customIt was purified by chromatographing on a silica gel column

Sources & evidence

ORD record
ord-ba344abf64eb4413ab59ff658fa578e0
Source dataset
uspto-grants-1986_05
Patent number
US04590202

Reaction notes

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