N,N'-Diethylthiourea → 2-[Ethylamino(ethylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

HRID 1702844Notes

Reaction equation

HRID 1702844 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:17]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[S:21])[CH3:18]>CC(C)=O>[ClH:1].[CH2:15]([O:14][C:12]([C:11]1[C:2]([S:21][C:20]([NH:22][CH2:23][CH3:24])=[N:19][CH2:17][CH3:18])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 2735009N,N'-DiethylthioureaHCID 12283436Ethyl 3-Chloroquinoxaline-2-carboxylate

Product 1

HCID 1317128362-[Ethylamino(ethylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-3-quinoxalinecarboxylic acid, ethyl ester (7.100 g., 0.03 mole) and 3.967 g., (0.03 mole) of 1,3-diethylthiourea were dissolved in 150 ml. of acetone and boiled in an open flask for 1 hour. The reaction mixture was stirred at room temperature for 1 hour, then concentrated to a volume of 50 ml. After standing at room temperature overnight, the mixture was filtered and the solid residue washed with acetone and ether. Recrystallized from a mixture of methanol, acetone and ether it gave 7.182 g. product, m.p. 144.5°-145° C.

Workup

  1. concentrationconcentrated to a volume of 50 ml
  2. waitAfter standing at room temperature overnight
  3. filtrationthe mixture was filtered
  4. washthe solid residue washed with acetone and ether
  5. customRecrystallized from a mixture of methanol, acetone and ether it
  6. customgave 7.182 g

Sources & evidence

ORD record
ord-dfd248e1cc2e41bc9f3fdac2c03a43c4
Source dataset
uspto-grants-1982_09
Patent number
US04349674

Reaction notes

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