2-(1H-imidazol-1-yl)ethanamine → (2-Imidazol-1-yl-ethyl)-xanthen-9-yl-amine

HRID 1605149Notes

Reaction equation

HRID 1605149 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.C(O[CH:13]1[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)(=O)C>C1C=CC=CC=1>[N:4]1([CH2:3][CH2:2][NH:1][CH:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[O:20][C:21]3[C:26]2=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

4

Reactant 2

HCID 4306672-(1H-imidazol-1-yl)ethanamineHCID 125434549-Acetoxyxanthene

Product 1

HCID 21549470(2-Imidazol-1-yl-ethyl)-xanthen-9-yl-amine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.86 g. of 1-(2-aminoethyl)imidazole and 4.0 g. of 9-acetoxyxanthene dissolved in 100 ml. of dry benzene was refluxed for 24 hours. After cooling the solution was washed with 5% aqueous sodium carbonate solution and water, then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was redissolved in ether and deposited white crystals which were filtered and recrystallized from benzene-hexane to give N-[2-(1-imidazolyl)ethyl]-9-xanthenylamine, m.p. 90°-92° C.

Workup

  1. temperatureAfter cooling the solution
  2. washwas washed with 5% aqueous sodium carbonate solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was redissolved in ether
  7. filtrationwere filtered
  8. customrecrystallized from benzene-hexane

Sources & evidence

ORD record
ord-d9c1f0fcf6174ea092421631ad5ac1c1
Source dataset
uspto-grants-1976_04
Patent number
US03949076

Reaction notes

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