Hydroxylamine → HCID 10925830, compound

HRID 1292712Notes

Reaction equation

HRID 1292712 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.[NH2:21][OH:22].[C:23](Cl)(=O)[CH:24]=[CH2:25].[OH2:28].Cl[CH2:30]Cl>>[CH3:30][N:21]([O:22][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)[C:23](=[O:28])[CH:24]=[CH2:25]

Participants

6

Reactant 5

HCID 787HydroxylamineHCID 962WaterHCID 6344Dichloromethane2×HCID 13140Acryloyl chlorideHCID 22991106HCID 22991106, compound

Product 1

HCID 10925830HCID 10925830, compound

Conditions

Temperature
0 °C

Procedure

Dry dichloromethane (50 mL) was added to N-Methyl,N-(tert-butyldiphenylsilyl)hydroxylamine to dissolve the hydroxylamine derivative. N,Ndiisopropylethylamine 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. additionN,Ndiisopropylethylamine was added
  2. customthe two layers were separated
  3. washThe organic layer was washed with 10% ammonium chloride, saturated bicarbonate solution, and brine
  4. dry with materialThe organic solution was then dried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography (silica gel)
  8. additiona mixture of hexane and ethyl acetate
  9. washto elute the compound
  10. customThe purification

Sources & evidence

ORD record
ord-482c6df128214fafa7a89e416480c337
Source dataset
uspto-grants-2007_07
Patent number
US07238339B2

Reaction notes

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