Hydrochloric Acid → HCID 15895951, compound

HRID 1953388Notes

Reaction equation

HRID 1953388 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.Cl.C(N)C[NH2:27]>CC(C)=O.C1(C)C=CC=CC=1>[NH2:27][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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 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 HCl. 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. temperatureThe mixture is then cooled in an ice bath
  7. filtrationsuction filtered
  8. dry with materialThe collected solid thiourea intermediate is dried on a vacuum line (16 h, 0.5 torr)
  9. temperatureheated
  10. temperatureat reflux for six hours
  11. customis not isolated
  12. temperatureThe solution is cooled
  13. filtrationfiltered
  14. washThe solids are washed with toluene (20 mL)
  15. customdried under vacuum

Sources & evidence

ORD record
ord-9945c7f36a7c4232a2a627a6e9fca60c
Source dataset
uspto-grants-2000_09
Patent number
US06117871

Reaction notes

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