Sodium Hydroxide → 5-(1-Methoxy-2-methylpropan-2-yl)-1,2-oxazol-3-amine

HRID 2412530Notes

Reaction equation

HRID 2412530 reaction equation
Cl.[NH2:2]O.[CH3:4][O:5][CH2:6][C:7]([C:10]([CH2:12][C:13]#[N:14])=[O:11])([CH3:9])[CH3:8].[OH-].[Na+]>O.C(O)C>[NH2:14][C:13]1[CH:12]=[C:10]([C:7]([CH2:6][O:5][CH3:4])([CH3:9])[CH3:8])[O:11][N:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 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 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 58.5 g of hydroxylamine hydrochloride in 88 ml of water was added drop-by-drop over a 10-minute period to a stirred, refluxing solution of 100.9 g of 2B and 33.7 g of sodium hydroxide in 950 ml of water and 740 ml of ethanol. The mixture was stirred and refluxed for a further 18 hours, then the ethanol was evaporated in a rotary evaporator. The aqueous residue was cooled and filtered. The solid was chromatographed over silica gel, using as eluent a 2:15:33 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane, to give 3-amino-5-(1-(methoxymethyl)-1-methylethyl)-1,2-oxazole (2C), as a cream-colored solid, m.p.: 96°-99° C.

Workup

  1. temperaturerefluxed for a further 18 hours
  2. customthe ethanol was evaporated in a rotary evaporator
  3. temperatureThe aqueous residue was cooled
  4. filtrationfiltered
  5. customThe solid was chromatographed over silica gel
  6. additionv:v mixture of tetrahydrofuran, ethyl acetate and hexane

Sources & evidence

ORD record
ord-0ebf328d74e84a8188a190537e277e5e
Source dataset
uspto-grants-1985_01
Patent number
US04493728

Reaction notes

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