Hydroxylamine → HCID 10925830, compound

HRID 1168111Notes

Reaction equation

HRID 1168111 reaction equation
CN([Si:4]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)O.N[OH:22].C([N:26]([CH2:30]C)C(C)C)(C)C.[C:32](Cl)(=[O:35])[CH:33]=[CH2:34]>ClCCl.O>[CH3:30][N:26]([O:22][Si:4]([C:17]([CH3:19])([CH3:20])[CH3:18])([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:32](=[O:35])[CH:33]=[CH2:34]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 22991106HCID 22991106, compound

Product 1

HCID 10925830HCID 10925830, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dry dichloromethane (50 mL) was added to N-Methyl,N-(tert-butyldiphenylsilyl)hydroxylamine to dissolve the hydroxylamine derivative. N,N-diisopropylethylamine was added. The resulting solution was stirred and cooled at 0° C. with an ice bath. Acryloyl chloride in 10 mL of dry dichloromethane was added. Then water was added and the two layers were separated. The organic layer was washed with 10% ammonium chloride, saturated bicarbonate solution, and brine. The organic solution was then dried with magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography (silica gel) using a mixture of hexane and ethyl acetate to elute the compound. The purification produced N-Methyl,N-(tert-butyldiphenylsilyloxy)acrylamide (28).

Workup

  1. customthe two layers were separated
  2. washThe organic layer was washed with 10% ammonium chloride, saturated bicarbonate solution, and brine
  3. dry with materialThe organic solution was then dried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash chromatography (silica gel)
  7. additiona mixture of hexane and ethyl acetate
  8. washto elute the compound
  9. customThe purification

Sources & evidence

ORD record
ord-6f12d1d3398e48eb9f414f5cf004b9ae
Source dataset
uspto-grants-2003_09
Patent number
US06623721B2

Reaction notes

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