Diethyl Ether → HCID 178419297, compound

HRID 280560Notes

Reaction equation

HRID 280560 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([NH2:16])[C:6]=2[CH:17]=1.[IH:18].CS[C:21]1[NH:22][CH2:23][CH2:24][N:25]=1.CCOCC>C(O)C>[IH:18].[NH:22]1[CH2:23][CH2:24][NH:25][C:21]1=[N:16][CH:7]1[C:6]2[CH:17]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[CH:11]=[CH:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]1=2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)HCID 13654285HCID 13654285, compound

Product 1

HCID 178419297HCID 178419297, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

6.90 grams (0.024 mole) of 3-bromo-5H-dibenzo[a,d]cycloheptene-5-ylamine, 2.95 grams (0.012 mole) of 2-methylmercapto-4,5-dihydroimidazole hydroiodide, and 65 milliliters of absolute ethanol were stirred together and refluxed for 28 hours. At the end of this period, the solvent was evaporated under reduced pressure and the residue triturated with five 100 milliliter portions of diethyl ether to obtain a purified residue. The purified residue was dissolved in 20 milliliters of absolute ethanol and 300 milliliters of ether added thereto whereupon a solid precipitated. The mixture was stirred thoroughly, the solvent decanted to obtain a residue which was placed on a Still-silica column and eluted with 5 percent methanol in chloroform. The eluted fractions were examined by thin layer chromatography (TLC), the homogeneous TLC fractions combined, and the solvent then vaporized to obtain the desired N-(2-imidazolidinylidene)-3-bromo-5H-dibenzo[a,d]cyclohepten-5-amine hydroiodide product as residue. The product was crystallized from chloroform to obtain purified product, m.p. 240°-241° C. (dec.). Elemental analyses were as follows: Calc'd for C18H17BrIN3 : C, 44.84; H, 3.55; N, 8.72. Found: C, 44.75; H, 3.48; N, 8.46.

Workup

  1. temperaturerefluxed for 28 hours
  2. customAt the end of this period, the solvent was evaporated under reduced pressure
  3. customthe residue triturated with five 100 milliliter portions of diethyl ether
  4. customto obtain a purified residue
  5. customwhereupon a solid precipitated
  6. customthe solvent decanted
  7. customto obtain a residue which
  8. washeluted with 5 percent methanol in chloroform

Sources & evidence

ORD record
ord-14b40ae38fae4d4791bfa17cd110aa55
Source dataset
uspto-grants-1986_05
Patent number
US04590202

Reaction notes

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