Hydroxyamine hydrochloride → HCID 136403415, compound

HRID 2082029Notes

Reaction equation

HRID 2082029 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=[CH:17][C:18](=O)[CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:6]=1)([CH3:4])[CH3:3].Cl.[NH2:29][OH:30].C([O-])(=O)C.[Na+]>>[CH3:3][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:14])([CH3:15])[CH3:13])[N:8]=[C:7]([CH:16]=[CH:17][C:18](=[N:29][OH:30])[CH2:19][O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:6]=1)([CH3:1])[CH3:4]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54454289HCID 54454289, compound

Product 1

HCID 136403415HCID 136403415, compoundYield 29%

Procedure

1-[4,6-Bis(1,1-dimethylethyl)-5-hydroxypyrimidin-2-yl]-4-phenoxy-1-butene-3-one (0.7 g, 1.9 mmol) is added to an ethanolic (50 mL) solution of hydroxylamine hydrochloride (1.3 g, 19 mmol) and sodium acetate (1.7 g, 20.9 mmol). The reaction mixture is stirred at room temperature under argon for 18 hours. The ethanol is evaporated under reduced pressure, and the remaining solid is partitioned between 20 mL of water and 20 mL of ethyl acetate. The layers are separated and the aqueous phase is washed with ethyl acetate (3×20 mL). The combined organic layers are washed with water (3×20 mL) and 20 mL of brine. Drying over MgSO4 followed by evaporation of solvent gives a yellow oil. Flash chromatography (silica, methylene chloride) followed by recrystallization from hexane gives 0.21 g (29%) of 1-[4,6-bis(1,1-dimethylethyl)-5-hydroxypyrimidin-2-yl]-4-phenoxy-1-butene-3-one oxime, mp 130°-135° C.

Workup

  1. customThe ethanol is evaporated under reduced pressure
  2. customthe remaining solid is partitioned between 20 mL of water and 20 mL of ethyl acetate
  3. customThe layers are separated
  4. washthe aqueous phase is washed with ethyl acetate (3×20 mL)
  5. washThe combined organic layers are washed with water (3×20 mL) and 20 mL of brine
  6. dry with materialDrying over MgSO4
  7. customfollowed by evaporation of solvent
  8. customgives a yellow oil
  9. customFlash chromatography (silica, methylene chloride) followed by recrystallization from hexane

Sources & evidence

ORD record
ord-33d3eab569c54cc2b79fb788cf099982
Source dataset
uspto-grants-1993_02
Patent number
US05187175

Reaction notes

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