Triethylamine → HCID 67468122, compound

HRID 1406278Notes

Reaction equation

HRID 1406278 reaction equation
Cl[CH:2](Cl)/[C:3](=[N:5]\[NH:6]S(C1C=CC(C)=CC=1)(=O)=O)/[CH3:4].C(N(CC)CC)C.[C:25]([Si:29]([CH3:35])([CH3:34])[O:30][CH2:31][CH2:32][NH2:33])([CH3:28])([CH3:27])[CH3:26]>CO>[C:25]([Si:29]([CH3:35])([CH3:34])[O:30][CH2:31][CH2:32][N:33]1[CH:2]=[C:3]([CH3:4])[N:5]=[N:6]1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneHCID 23441517HCID 23441517, compound

Product 1

HCID 67468122HCID 67468122, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of N′-[(1Z)-2,2-dichloro-1-methylethylidene]-4-methylbenzenesulfonohydrazide (prepared according to WO2007088478 example 13) (5.0 g, 16.9 mmol) in methanol (100 mL), at 0° C. under an atmosphere of nitrogen, was added triethylamine (11.8 mL, 84.7 mmol, 5.0 eq.) over a period of 2 min. To the resulting orange solution was added a solution of 2-{[tert-butyl-(dimethyl)silyl]oxy}ethanamine (prepared according to J.O.C. 74(4), 1791-1793, 2009) (3.3 g, 18.8 mmol, 1.1 eq.) in methanol (70 ml). The reaction mixture was stirred at room temperature for 18 hr. The mixture was then evaporated under reduced pressure and the residue partitioned between tert-butyl methyl ether (250 mL) and aqueous citric acid (10% wt/vol, 100 mL). The organic phase was washed with aqueous sodium hydrogen carbonate (1M, 100 mL), saturated brine (20 mL) and dried over sodium sulphate. The resulting mixture was filtered and the filtrate concentrated under reduced pressure to give a crude brown oil. The crude oil was purified by chromatography on silica gel (200 g) eluting with a gradient of tert-butyl methyl ether in toluene (10:90 to 40:60) to give the title compound as a yellow oil (3.07 g, 75%).

Workup

  1. customThe mixture was then evaporated under reduced pressure
  2. customthe residue partitioned between tert-butyl methyl ether (250 mL) and aqueous citric acid (10% wt/vol, 100 mL)
  3. washThe organic phase was washed with aqueous sodium hydrogen carbonate (1M, 100 mL), saturated brine (20 mL)
  4. dry with materialdried over sodium sulphate
  5. filtrationThe resulting mixture was filtered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customto give a crude brown oil
  8. customThe crude oil was purified by chromatography on silica gel (200 g)
  9. washeluting with a gradient of tert-butyl methyl ether in toluene (10:90 to 40:60)

Sources & evidence

ORD record
ord-1fafdf925909452a9d72c8f10a0e308b
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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