Diisopropylethylamine → HCID 59168122, compound

HRID 1444072Notes

Reaction equation

HRID 1444072 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[N:17][C:16]([CH2:21][OH:22])=[CH:15][N:14]=1)(=[O:11])=[O:10].C(N(C(C)C)CC)(C)C.[CH3:32][Si:33]([CH3:40])([CH3:39])[CH2:34][CH2:35][O:36][CH2:37]Cl>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([C:13]1[C:18]([O:19][CH3:20])=[N:17][C:16]([CH2:21][OH:22])=[CH:15][N:14]=1)[CH2:37][O:36][CH2:35][CH2:34][Si:33]([CH3:40])([CH3:39])[CH3:32])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 58597374HCID 58597374, compound

Product 1

HCID 59168122HCID 59168122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2,3-dichloro-N-[5-(hydroxymethyl)-3-methoxy-2-pyrazinyl]-benzenesulphonamide (1.0 g) in dichloromethane (100 mL) was added diisopropylethylamine (0.57 mL) and 2-(trimethylsilyl)ethoxymethyl chloride (0.58 mL). The reaction mixture was stirred at room temperature for 0.5 h, then washed with water. The organic phase was dried (MgSO4), filtered and evaporated to give a yellow oil. This was purified by chromatography on silica gel eluting with dichloromethane/ethyl acetate mixtures to give the title compound as a colourless oil (0.8 g).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give a yellow oil
  6. customThis was purified by chromatography on silica gel eluting with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-72c2fd3efb924a3084d438b11542f482
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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