Ethanolamine → HCID 10287407, compound

HRID 1444020Notes

Reaction equation

HRID 1444020 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([C:21]1[C:26]([O:27][CH3:28])=[N:25][C:24](Cl)=[CH:23][N:22]=1)COCC[Si](C)(C)C)(=[O:11])=[O:10].[CH2:30]([CH2:32][NH2:33])[OH:31].[H-].[Na+]>COCCOC>[NH2:33][CH2:32][CH2:30][O:31][C:24]1[N:25]=[C:26]([O:27][CH3:28])[C:21]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])(=[O:10])=[O:11])=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 24758Sodium hydrideHCID 11271967HCID 11271967, compound

Product 1

HCID 10287407HCID 10287407, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2,3-Dichloro-N-(5-chloro-3-methoxy-2-pyrazinyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulphonamide (Example 115a) (0.25 g) was added to a mixture of ethanolamine (0.05 mL) and sodium hydride (0.035 g of a 60% dispersion in oil) in 1,2-dimethoxyethane (15 mL) at room temperature. After 2 h, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. Chromatography on silica gel eluting with methanol/dichloromethane mixtures gave the title compound containing the SEM ([2-(trimethylsilyl)ethoxy]methyl) protecting group as an oil (0.14 g). Trifluoroacetic acid (1 mL) and dichloromethane (3 mL) were added. After 0.5 h at room temperature, toluene was added and the solution evaporated to dryness. HCl (4M in dioxane) was added and the mixture evaporated to dryness. The product was crystallised from diethyl ether (0.075 g).

Workup

  1. customthe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6d091f497c764875ab7c151a83edf661
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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