Ethylenediamine → HCID 15895951, compound

HRID 355730Notes

Reaction equation

HRID 355730 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=O)[C:2]1C=CC=CC=1.[NH2:12][C:13]1[C:14]([CH3:23])=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[N:16]2.C(N)C[NH2:26]>CC(C)=O.C1(C)C=CC=CC=1>[NH2:26][CH2:2][CH2:1][NH:9][C:10](=[S:11])[NH:12][C:13]1[C:14]([CH3:23])=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[N:16]2

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 68284Benzoyl isothiocyanateHCID 15895950HCID 15895950, compound

Product 1

HCID 15895951HCID 15895951, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 1140TolueneSolvent

Procedure

To a refluxing solution of benzoyl isothiocyanate (1.6 g) in dry acetone (20 mL) is added dropwise a solution of 6-amino-5-methylquinoxaline (1.2 g) in dry acetone (50 mL) over 30 minutes. The mixture is refluxed an additional two hours, cooled to room temperature, and rotary evaporated to a residue. This material is suspended in 10% NaOH solution (50 mL) forming a mixture which is heated at 90° C. for 30 minutes, then cooled to room temperature and adjusted to pH=8 by adding concentrated HCI. The mixture is then cooled in an ice bath and suction filtered. The collected solid thiourea intermediate is dried on a vacuum line (16 h, 0.5 torr), suspended in bromobenzene (50 mL) and heated at reflux for six hours to effect conversion to the isothiocyanate intermediate which is not isolated. The solution is cooled, then added dropwise to a solution of ethylene diamine (5.0 mL) in toluene (10 mL). The resulting mixture is stirred for 16 hours and filtered. The solids are washed with toluene (20 mL) and dried under vacuum to yield 6-(N'-aminoethylthioureido)-5-methylquinoxaline.

Workup

  1. temperatureThe mixture is refluxed an additional two hours
  2. customrotary evaporated to a residue
  3. customforming a mixture which
  4. temperatureis heated at 90° C. for 30 minutes
  5. temperaturecooled to room temperature
  6. additionby adding
  7. concentrationconcentrated HCI
  8. temperatureThe mixture is then cooled in an ice bath
  9. filtrationsuction filtered
  10. dry with materialThe collected solid thiourea intermediate is dried on a vacuum line (16 h, 0.5 torr)
  11. temperatureheated
  12. temperatureat reflux for six hours
  13. customis not isolated
  14. temperatureThe solution is cooled
  15. filtrationfiltered
  16. washThe solids are washed with toluene (20 mL)
  17. customdried under vacuum

Sources & evidence

ORD record
ord-17192f2b35974cfe965ece5f6655b551
Source dataset
uspto-grants-1998_11
Patent number
US05834470

Reaction notes

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