Diisopropylethylamine → N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

HRID 1443976Notes

Reaction equation

HRID 1443976 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([O:20][CH3:21])[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:11])=[O:10])=[N:6][CH:7]=1.[CH:22](N([CH:28]([CH3:30])C)CC)(C)C.Cl[CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37]>ClCCl>[C:4]([O:20][CH2:28][CH3:30])(=[O:33])[CH3:5].[CH3:12][CH2:17][CH2:16][CH:15]([CH3:14])[CH3:22].[Br:1][C:2]1[N:3]=[C:4]([O:20][CH3:21])[C:5]([N:8]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:10])=[O:11])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10309893N-(5-bromo-3-methoxypyrazinyl)-2,3-dichlorobenzenesulfonamide

Product 2

HCID 21882781Isohexane ethyl acetateHCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamideYield 152.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichlorobenzenesulphonamide (Example 8) (0.40 g), diisopropylethylamine (0.26 g) and [2-(chloromethoxy)ethyl]trimethylsilane (0.25 g) in dichloromethane (50 mL) was stirred at room temperature. After 2 h, the solution was washed with water, dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound as a white solid (0.40 g).

Workup

  1. washthe solution was washed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-fccdade5eb9244c29b5d4b135c145625
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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