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

HRID 336205Notes

Reaction equation

HRID 336205 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 to afford 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

Sources & evidence

ORD record
ord-5d7650c304ed46899244e289cd09a126
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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