Triethylamine → 1,2-Dihydro-8-(4-(methylsulphonyl)piperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxide

HRID 2309692Notes

Reaction equation

HRID 2309692 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]1([C:19]2[C:20]3[N:21]([CH2:36][CH2:37][N:38]=3)[C:22]3[C:27]([N+:28]=2[O-:29])=[CH:26][CH:25]=[C:24]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:23]=3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH3:1][S:2]([N:33]1[CH2:34][CH2:35][N:30]([C:24]2[CH:23]=[C:22]3[C:27]([N+:28]([O-:29])=[C:19]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:20]4[N:21]3[CH2:36][CH2:37][N:38]=4)=[CH:26][CH:25]=2)[CH2:31][CH2:32]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 99501581,2-Dihydro-4-phenyl-8-piperazinylimidazo[1,2-a]quinoxaline 5-oxide

Product 1

HCID 139586181,2-Dihydro-8-(4-(methylsulphonyl)piperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxideYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (0.33 g, 0.003 mol) in dichloromethane (20 ml) was cooled in an ice-bath. To this solution was added dropwise with stirring, a solution of triethylamine (0.29 g, 0.003 mol) and 1,2-dihydro-4-phenyl-8-piperazinylimidazo[1,2-a]quinoxaline 5-oxide (1 g, 0.003 mol) in dichloromethane (10 ml). The reaction mixture was stirred for an additional 15 minutes and then was allowed to warm to room temperature. The reaction mixture was washed with water, dried over anhydrous magnesium sulphate and then evaporated to dryness under reduced pressure to yield a yellow solid. Recrystallization from ethyl acetate yielded 1,2-dihydro-8-(4-(methylsulphonyl)piperazinyl)-4-phenylimidazo[1,2-a]quinoxaline 5-oxide (0.8 g), as yellow crystals, m.p. 252°-253° C. (Found: C,59.19; H,5.35; N,16.33%; C21H23N5O3S requires C,59.29; H,5.41; N,16.47%) having the formula: ##STR31##

Workup

  1. additionTo this solution was added dropwise
  2. stirringThe reaction mixture was stirred for an additional 15 minutes
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. customto yield a yellow solid
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-aee75739d7a44804a0cf00254b452c24
Source dataset
uspto-grants-1987_09
Patent number
US04696928

Reaction notes

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