Acetic Acid → (Methylamino(methylamino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

HRID 1702843Notes

Reaction equation

HRID 1702843 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.[CH3:17][NH:18][C:19]([NH:21][CH3:22])=[S:20].C(O)(=O)C>CC(C)=O>[ClH:1].[CH2:15]([O:14][C:12]([C:11]1[C:2]([S:20][CH:19]([NH:21][CH3:22])[NH:18][CH3:17])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723631N,N'-DimethylthioureaHCID 12283436Ethyl 3-Chloroquinoxaline-2-carboxylate

Product 1

HCID 131712834(Methylamino(methylamino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-3-quinoxalinecarboxylic acid, ethyl ester (4.733 g., 0.02 mole) and 2.084 g., (0.02 mole) of N,N'-dimethylthiourea were dissolved in a solution of 10 ml. of acetic acid and 90 ml. of acetone. The mixture was heated at reflux for 1 hour, cooled in an icebath and filtered. The residue was washed with acetone, triturated with two portions of acetonitrile, washed with ether, and dried to give 4.70 g. of the product, m.p. 162°-163.5° (dec.)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled in an icebath
  4. filtrationfiltered
  5. washThe residue was washed with acetone
  6. customtriturated with two portions of acetonitrile
  7. washwashed with ether
  8. customdried
  9. customto give 4.70 g

Sources & evidence

ORD record
ord-38d9f94a920d48fbb9ec12d73222bb20
Source dataset
uspto-grants-1982_09
Patent number
US04349674

Reaction notes

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