Water → HCID 15638264, compound

HRID 1168112Notes

Reaction equation

HRID 1168112 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].Cl.[CH2:7]([O:14][NH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)C(C)C)(C)C.O>ClCCl>[CH2:7]([O:14][NH:15][C:1](=[O:4])[CH:2]=[CH2:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 15638264HCID 15638264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of acryloyl chloride dissolved in dry dichloromethane was cooled at 0° C. with an ice bath. A mixture of O-benzyl hydroxylamine hydrochloride (29) and N,N-diisopropylethylamine in dry dichloromethane was added. Water was added and the layers were separated. The organic solution was washed with diluted hydrochloric acid, a saturated sodium bicarbonate solution, water, and brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by flash chromatography using a mixture of hexane and ethyl acetate. The purification gave N-benzyloxyacrylamide (30).

Workup

  1. additionwas added
  2. customthe layers were separated
  3. washThe organic solution was washed with diluted hydrochloric acid
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. additiona mixture of hexane and ethyl acetate
  9. customThe purification

Sources & evidence

ORD record
ord-082a2a8217054b69a6b86c0e5644b781
Source dataset
uspto-grants-2003_09
Patent number
US06623721B2

Reaction notes

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