Acetone → 2-[(1-Methylethylamino)(1-methylethylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

HRID 1702845Notes

Reaction equation

HRID 1702845 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].[CH:17]([NH:20][C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[S:22])([CH3:19])[CH3:18].CC(C)=O>C(O)(=O)C>[ClH:16].[CH2:1]([O:3][C:4]([C:6]1[C:7]([S:22][C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[N:20][CH:17]([CH3:19])[CH3:18])=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 2758386DiisopropylthioureaHCID 12283436Ethyl 3-Chloroquinoxaline-2-carboxylate

Product 1

HCID 1317128372-[(1-Methylethylamino)(1-methylethylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (4.73 g., 0.02 mole) and 3.206 g. (0.02 mole) of 1,3-diisopropylthiourea were dissolved in 90 ml. of acetone and 10 ml. of acetic acid. The solution was heated on the steambath for 23/4 hours and filtered hot. The solvent in the filtrate was evaporated and the residue was triturated with ether until it solidified. Filtration gave 2.33 g. of crude product. Recrystallized from acetone-ether it afforded 1.28 g. (16.1%) of a yellow solid, m.p. 148°-149° C. (dec).

Workup

  1. temperatureThe solution was heated on the steambath for 23/4 hours
  2. filtrationfiltered hot
  3. customThe solvent in the filtrate was evaporated
  4. customthe residue was triturated with ether until it
  5. filtrationFiltration
  6. customgave 2.33 g
  7. customRecrystallized from acetone-ether it
  8. customafforded 1.28 g

Sources & evidence

ORD record
ord-35e1f1ff6c0a4bc4b20130f47d591929
Source dataset
uspto-grants-1982_09
Patent number
US04349674

Reaction notes

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