1,3-Dipropyl-2-thiourea → 2-[(Propylamino)(propylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

HRID 1702846Notes

Reaction equation

HRID 1702846 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([Cl:16])=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].[CH2:17]([NH:20][C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[S:22])[CH2:18][CH3:19]>CC(C)=O>[ClH:16].[CH2:1]([O:3][C:4]([C:6]1[C:7]([S:22][C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[N:20][CH2:17][CH2:18][CH3:19])=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 28012141,3-Dipropyl-2-thioureaHCID 12283436Ethyl 3-Chloroquinoxaline-2-carboxylate

Product 1

HCID 1317128382-[(Propylamino)(propylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (3.551 g., 0.015 mole) and 2.405 g. (0.015 mole) of 1,3-di-n-propylthiourea were dissolved in acetone and heated at reflux for 11/2 hours. The solution was concentrated to a volume of 50 ml. and cooled. A small amount of solid was removed by filtration. The filtrate was further concentrated to a volume of 25 ml. and ether was added to turbidity. After the reaction mixture had been cooled the yellow solid was collected by filtration to give 2.77 g. (46.6%) of the product, m.p. 129°-130° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 11/2 hours
  3. concentrationThe solution was concentrated to a volume of 50 ml
  4. temperatureand cooled
  5. customA small amount of solid was removed by filtration
  6. concentrationThe filtrate was further concentrated to a volume of 25 ml
  7. additionand ether was added to turbidity
  8. temperatureAfter the reaction mixture had been cooled the yellow solid
  9. filtrationwas collected by filtration
  10. customto give 2.77 g

Sources & evidence

ORD record
ord-fa6568838bfc4132b2fd45d569acd97c
Source dataset
uspto-grants-1982_09
Patent number
US04349674

Reaction notes

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