O-Methylhydroxylamine hydrochloride → HCID 24959928, compound

HRID 2092506Notes

Reaction equation

HRID 2092506 reaction equation
[F:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=O.Cl.[CH3:22][O:23][NH2:24]>S(Cl)(Cl)=O>[F:18][C:17]([F:20])([F:19])[S:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([C:2]([F:1])([CH3:6])[C:3]([NH:24][O:23][CH3:22])=[O:5])=[CH:8][CH:9]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 24959562HCID 24959562, compound

Product 1

HCID 24959928HCID 24959928, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 1 (0.5 gr, 1.6 mmol) in thionyl chloride (5 mL) was refluxed for 3 h. After cooling at room temperature, thionyl chloride was evaporated under vacuum and the crude acyl chloride was diluted in dry CH2Cl2 (5 mL) and cooled at T=0° C. by ice-water bath. Methoxyamine hydrochloride (0.27 g, 3.2 mmol) was added portionwise. The ice-water bath was removed and the reaction mixture was left stirring at room temperature. After complete disappearance of the starting material (TLC) a buffer solution (pH=2.0) (V=10 ml) was added, the two phases trasferred into a separator funnel and separated and the organic one was washed with brine (3×10 mL), dried over Na2SO4 and evaporated under vacuum to give pure 11 as pale yellow oil (0.47 gr, yield 85%). 1H-NMR (CDCl3) δ 9.05 (bs, 1H, CONH), 7.70 (d, 2H, J=7 Hz), 7.30 (d, 2H, J=7 Hz), 3.80 (s, 3H), 1.95 (d, 3H, J=23 Hz).

Workup

  1. temperaturewas refluxed for 3 h
  2. customthionyl chloride was evaporated under vacuum
  3. additionthe crude acyl chloride was diluted in dry CH2Cl2 (5 mL)
  4. temperaturecooled at T=0° C. by ice-water bath
  5. customThe ice-water bath was removed
  6. waitthe reaction mixture was left
  7. additionAfter complete disappearance of the starting material (TLC) a buffer solution (pH=2.0) (V=10 ml) was added
  8. customthe two phases trasferred into a separator funnel
  9. customseparated
  10. washthe organic one was washed with brine (3×10 mL)
  11. dry with materialdried over Na2SO4
  12. customevaporated under vacuum

Sources & evidence

ORD record
ord-3ddc56c3ad2141a5a9b4c42a2da7ac0f
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

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