N-methylhydroxylamine hydrochloride → HCID 86753360, compound

HRID 1417092Notes

Reaction equation

HRID 1417092 reaction equation
Cl.[CH3:2][NH:3][OH:4].CC(C)([O-])C.[K+].CS(O[CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:29][CH2:28][C:27]3[CH:30]=[CH:31][S:32][C:26]=3[C:25](=[O:33])[C:24]=2[CH:34]=1)(=O)=O>C(O)C>[O:33]=[C:25]1[C:24]2[CH:34]=[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][N:3]([OH:4])[CH3:2])[CH:21]=[CH:22][C:23]=2[O:29][CH2:28][C:27]2[CH:30]=[CH:31][S:32][C:26]1=2

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 88429211HCID 88429211, compound

Product 1

HCID 86753360HCID 86753360, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirring solution of 4.77 g of N-methylhydroxylamine hydrochloride in 100 ml of absolute ethanol was added 6.38 g of potassium tert-butoxide. To the resulting suspension was added 6.98 g of 4-(4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-yl)butanol methanesulfonate, and an additional 150 ml of absolute ethanol. The suspension was allowed to reflux for 24 hours and was then cooled to room temperature. The suspension was filtered to remove potassium chloride and the filter cake was washed with absolute ethanol. The resulting solution was concentrated in vacuo to a waxy solid. The solid was dissolved in 300 ml of methylene chloride and partitioned against 200 ml of water. The organic phase was dried with 200 ml of saturated aqueous sodium chloride, collected, dried again (Na2SO4), filtered, and concentrated in vacuo to an oil. The oil solidified upon standing, and was recrystallized from isopropanol to give 3.09 g of 4-(4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-yl)-N-hydroxy-N-methyl-1-butylamine, m.p. 107-108° C.

Workup

  1. temperatureto reflux for 24 hours
  2. filtrationThe suspension was filtered
  3. customto remove potassium chloride
  4. washthe filter cake was washed with absolute ethanol
  5. concentrationThe resulting solution was concentrated in vacuo to a waxy solid
  6. dissolutionThe solid was dissolved in 300 ml of methylene chloride
  7. custompartitioned against 200 ml of water
  8. dry with materialThe organic phase was dried with 200 ml of saturated aqueous sodium chloride
  9. customcollected
  10. dry with materialdried again (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo to an oil
  13. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-e74bfc0c65174043997d25ecb9996bf6
Source dataset
uspto-grants-1999_06
Patent number
US05917057

Reaction notes

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