2-(1H-imidazol-1-yl)ethanamine → HCID 178477864, compound

HRID 580863Notes

Reaction equation

HRID 580863 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8](=S)[NH:7][C:6]=2[CH:17]=1.[NH2:18][CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>C(OCCO)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([NH:18][CH2:19][CH2:20][N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)=[N:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 4306672-(1H-imidazol-1-yl)ethanamineHCID 125357788-Chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione

Product 1

HCID 178477864HCID 178477864, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.6 g (2.3 mmol) of 8-chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione in 15 mL of 2-ethoxyethanol was treated with 0.6 mL (4.6 mmol) of 1-(2-aminoethyl)imidazole and heated at reflux for 2 days. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed three times with H2O, then saturated NaHCO3 solution, and saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. This was recrystallized from EtOAc/hexane using charcoal to give 0.44 g (57.1% yield) of the product as pale yellow crystals, mp 168-170° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =338.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 days
  3. customThe solvent was removed under reduced pressure
  4. washwashed three times with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. waitleft the crude product
  7. customThis was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-5b925a6dbad44516b076de80e86a116d
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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