Water → HCID 11180148, compound

HRID 1443986Notes

Reaction equation

HRID 1443986 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]([Cl:21])=[C:15]([Cl:22])[N:14]=1)(=[O:11])=[O:10].[CH2:23](N([CH2:28][CH3:29])CC)C.[CH3:30][Si:31]([CH3:38])([CH3:37])[CH2:32][CH2:33][O:34][CH2:35]Cl.O>ClCCl>[C:18]([O:19][CH2:28][CH3:29])(=[O:34])[CH3:13].[CH3:4][CH2:5][CH2:6][CH:7]([CH3:2])[CH3:23].[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]([Cl:21])=[C:15]([Cl:22])[N:14]=1)[CH2:35][O:34][CH2:33][CH2:32][Si:31]([CH3:38])([CH3:37])[CH3:30])(=[O:10])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10216192HCID 10216192, compound

Product 2

HCID 11180148HCID 11180148, compoundHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,3-Dichloro-N-(5,6-dichloro-3-methoxy-2-pyrazinyl)benzenesulphonamide (0.68 g) in dichloromethane (20 mL) was added triethylamine (0.49 mL) followed by 2-(trimethylsilyl)ethoxymethyl chloride (0.328 g) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water (50 mL) and extracted into ethyl acetate (3×20 mL). The combined extracts were dried (MgSO4), filtered and concentrated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the sub-title compound as a white solid (0.74 g).

Workup

  1. extractionextracted into ethyl acetate (3×20 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c270f514e60c47c9a66590f9bc43248f
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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