Diethylamine → HCID 4692354, compound

HRID 1954703Notes

Reaction equation

HRID 1954703 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16]>C(O)C>[CH2:15]([N:17]([CH2:18][CH3:19])[C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:16]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 107745254-chloroimidazo[1,2-a]quinoxaline

Product 1

HCID 4692354HCID 4692354, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,8 g of 4-chloroimidazo[1,2-a]quinoxaline (example 1) and 9.8 ml of diethylamine in 40 ml of ethanol is refluxed for 4 h. After evaporating the solvent, the residue is taken up in chloroform and washed with water and saturated NaCl, then dried and evaporated, thereby obtaining 2.2 g of raw product that is subsequently chromatographed on SiO2 (eluent: CH2Cl2): after recrystallization from n-hexane there are obtained 1.3 g of 4- diethylaminoimidazo[1,2-a]quinoxaline. m.p. (DSC)=91.7° C. (onset); IR (KBr): 2976, 1518, 1425, cm-1 ; 1H-NMR (CDCl3): δ7.9 (1H,s), 7.7÷7.4 (3H,m), 7.35÷7.05 (2H,m), 4.15 (4H,q), 1.3 (6H,t); UV (EtOH): λmax =231, 250, 293, 305, 332, 348 nm. Elementary analysis for C14H16N4 (m.w. 240.31): calcd. C 69.97, H 6.71, N 23.31%; found C 69.99, H 6.80, N 23.13%.

Workup

  1. temperatureis refluxed for 4 h
  2. customAfter evaporating the solvent
  3. washwashed with water and saturated NaCl
  4. customdried
  5. customevaporated
  6. customobtaining 2.2 g of raw product that
  7. customis subsequently chromatographed on SiO2 (eluent: CH2Cl2)
  8. customafter recrystallization from n-hexane

Sources & evidence

ORD record
ord-a3ebe7e0fe7c4cbfa38e87998302a7e0
Source dataset
uspto-grants-2000_09
Patent number
US06124287

Reaction notes

Loading…