Sodium hydride → [5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl][(2,3-dichlorophenyl)sulphonyl]carbamic acid, 2-methylpropyl ester

HRID 1444040Notes

Reaction equation

HRID 1444040 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[C:6]([O:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])(=[O:13])=[O:12])=[N:8][CH:9]=1.[CH2:30]([O:34][C:35](Cl)=[O:36])[CH:31]([CH3:33])[CH3:32]>COCCOC>[Br:3][C:4]1[N:5]=[C:6]([O:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:7]([N:10]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])(=[O:12])=[O:13])[C:35](=[O:36])[O:34][CH2:30][CH:31]([CH3:33])[CH3:32])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62365Isobutyl chloroformateHCID 10239030N-[5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl]-2,3-dichlorobenzenesulphonamide

Product 1

HCID 58597367[5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl][(2,3-dichlorophenyl)sulphonyl]carbamic acid, 2-methylpropyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (0.045 g of a 60% dispersion in oil) was added to N-[5-bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl]-2,3-dichlorobenzenesulphonamide (Example 34) (0.5 g) in 1,2-dimethoxyethane (3 mL). Iso-butylchloroformate (0.15 mL) was added. After 2 h, the mixture was partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) and evaproated to yield the product (0.65 g). Used directly.

Workup

  1. customthe mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)

Sources & evidence

ORD record
ord-3c01d956baca4d299b718e4a95db3411
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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