Triethylamine → 7-(5-Chloro-2-methoxyphenyl)-8-chloromethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871976Notes

Reaction equation

HRID 871976 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8]2[C:17]([CH2:18]O)=[C:16]3[C:11]([NH:12][C:13]([CH3:23])([CH3:22])[C:14](=[O:21])[N:15]3[CH3:20])=[CH:10][CH:9]=2)[CH:7]=1.C(N(CC)CC)C.CS([Cl:37])(=O)=O.C(OCC)(=O)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8]2[C:17]([CH2:18][Cl:37])=[C:16]3[C:11]([NH:12][C:13]([CH3:22])([CH3:23])[C:14](=[O:21])[N:15]3[CH3:20])=[CH:10][CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 576717857-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 576717647-(5-Chloro-2-methoxyphenyl)-8-chloromethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(5-Chloro-2-methoxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 13-1, 1.34 g, 3.71 mmol) was dissolved in anhydrous dichloromethane (19 mL), and triethylamine (621 μL, 4.46 mmol) and methanesulfonyl chloride (316 μL, 4.08 mmol) were added thereto successively. The reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added to the reaction mixture, washed with water (200 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.14 g) as a colorless amorphous product. (Yield 81%)

Workup

  1. washwashed with water (200 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-24505f1017e6472482e9861579dc86e9
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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