Triethylamine → HCID 10560736, compound

HRID 1954702Notes

Reaction equation

HRID 1954702 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:13]([NH2:16])[C:14]#[CH:15].C(N(CC)CC)C>C(O)C>[Cl:12][C:11]1[C:2]([NH:16][CH2:13][C:14]#[CH:15])=[N:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166592,3-DichloroquinoxalineHCID 239041Propargylamine

Product 1

HCID 10560736HCID 10560736, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g of 2,3-dichloroquinoxaline, 4.5 ml of propargylamine, 10.5 ml of triethylamine in 50 ml of ethanol is refluxed for 4 h. After evaporating under vacuum the resulting mixture, the residue is chromatographed on SiO2 (eluent: CH2Cl2) thereby obtaining 7.0 g of 2-chloro-3-(propargylamino)quinoxaline (IR (KBr): 3441, 3282, 1518 cm-1). This product is then added with 10 ml of concentrated sulphuric acid and the resulting mixture is stirred at 90° C. for 1 h. After cooling down and cautiously neutralizing with aqueous NaOH, the resulting precipitate is filtered under vacuum, washed, dried, decolorized and recrystallized from dimethylformamide, thereby obtaining 2.4 g of 1-methylimidazo[1,2-a]quinoxaline-4(5H)-one (m.p. >300° C.).

Workup

  1. temperatureis refluxed for 4 h
  2. customAfter evaporating under vacuum the resulting mixture
  3. customthe residue is chromatographed on SiO2 (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-72b6dfe5bc6c4e07ac6106d26e528101
Source dataset
uspto-grants-2000_09
Patent number
US06124287

Reaction notes

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