Hydrochloric Acid → 5-(1-Methoxy-2-methylpropan-2-yl)-1,2-oxazol-3-amine

HRID 469759Notes

Reaction equation

HRID 469759 reaction equation
S(O)(O)(=O)=O.[NH2:6]O.[CH3:8][O:9][CH2:10][C:11]([CH3:18])([CH3:17])[C:12](=[O:16])[CH2:13][C:14]#[N:15].[OH-].[Na+].Cl>O>[CH3:8][O:9][CH2:10][C:11]([C:12]1[O:16][N:15]=[C:14]([NH2:6])[CH:13]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 159255Hydroxylamine, sulfate (1:1)HCID 108989285-Methoxy-4,4-dimethyl-3-oxopentanenitrile

Product 1

HCID 133396145-(1-Methoxy-2-methylpropan-2-yl)-1,2-oxazol-3-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of hydroxylamine sulfate (976 mg, 5.947 mmol) in water (4 mL) is added to a stirred solution of 5-methoxy-4,4-dimethyl-3-oxo-pentanenitrile (1.678 g, 10.812 mmol) and sodium hydroxide (490.3 mg, 11.89 mmol) in water (13 mL). The reaction mixture is heated to reflux over 30 minutes and kept at reflux for 1 hour. After cooling, 37% HCl aqueous solution (0.8 mL, 9.73 mmol) is added and the mixture is heated to reflux for 20 minutes. After cooling, the mixture's pH is adjusted to ˜12 by adding 40% sodium hydroxide aqueous solution. The mixture is extracted with methylene chloride 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 171 [M+H+].

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux over 30 minutes
  3. temperatureat reflux for 1 hour
  4. temperatureAfter cooling
  5. temperaturethe mixture is heated
  6. temperatureto reflux for 20 minutes
  7. temperatureAfter cooling
  8. extractionThe mixture is extracted with methylene chloride 3 times
  9. washwashed with brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4bb03a0d06254c37ad4985f70308ad2a
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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