Methanethiol → 4-(Methylthio)pyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester

HRID 65775Notes

Reaction equation

HRID 65775 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11](Cl)[C:10]=12)=[O:5])[CH3:2].[Na].[CH3:21][SH:22].O>CN(C)C=O>[CH3:21][S:22][C:11]1[C:10]2[N:9]([N:8]=[CH:7][C:6]=2[C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:18]2[C:13]([N:12]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 5360545SodiumHCID 54256020Ethyl 4-chloropyrazolo[1,5-A]quinoxaline-3-carboxylate

Product 1

HCID 859214804-(Methylthio)pyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.76 g. of 4-chloropyrazolo[1,5-a]quinoxaline-3-carboxylic acid ethyl ester are heated with 0.71 g. of the sodium salt of methyl mercaptan in dimethylformamide. After cooling, the reaction mixture is poured into water. The product 4-(methylthio)pyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester is filtered under suction and crystallized from ethanol as white needles, m.p. 97°-98°.

Workup

  1. temperatureAfter cooling
  2. filtrationThe product 4-(methylthio)pyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester is filtered under suction
  3. customcrystallized from ethanol as white needles, m.p. 97°-98°

Sources & evidence

ORD record
ord-ef3ebaadc5f24369824fc28e65200787
Source dataset
uspto-grants-1978_12
Patent number
US04128716

Reaction notes

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