tert-Butylacrylamide → HCID 14297377, compound

HRID 345514

Reaction equation

HRID 345514 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:23]([NH:27][C:28](=[O:31])[CH:29]=[CH2:30])([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[C:23]([NH:27][C:28](=[O:31])[CH2:29][CH2:30][O:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 7877tert-ButylacrylamideHCID 69297DibenzylhydroxylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 14297377HCID 14297377, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 21.33 g of dibenzylhydroxylamine in 100 ml of dry tetrahydrofuran is admixed with 1.12 g of potassium-tert-butoxide followed by 12.70 g of N-tert-butylacrylamide. The solution is heated under reflux for 24 hours under N2. The crude reaction mixture is concentrated under reduced pressure and the residue is partitioned between water and methylene chloride. The organic layer is washed with water, brine dried (MgSO4) and evaporated under reduced pressure. Purification by liquid chromatography affords the title compound as an oil.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 24 hours under N2
  3. customThe crude reaction mixture
  4. concentrationis concentrated under reduced pressure
  5. customthe residue is partitioned between water and methylene chloride
  6. washThe organic layer is washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customPurification by liquid chromatography

Sources & evidence

ORD record
ord-93ff27e0422a4cc28e2a15a9a0978d7d
Source dataset
uspto-grants-1991_10
Patent number
US05057563

Linked notes

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