2-Amino-2-methyl-1-propanol → HCID 21264915, compound

HRID 464767Notes

Reaction equation

HRID 464767 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]([C:13]([O:15][CH3:16])=[O:14])#[C:8][C:9]([O:11][CH3:12])=[O:10]>C(O)C>[CH3:5][C:2]1([CH3:6])[CH2:3][O:4][C:13](=[O:14])[C:7](=[CH:8][C:9]([O:11][CH3:12])=[O:10])[NH:1]1.[O:15]1[CH:16]=[CH:2][N:1]=[CH:7][C:13]1=[O:14]

Participants

5

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 12980Dimethyl acetylenedicarboxylate

Product 2

HCID 21264915HCID 21264915, compoundHCID 70453060HCID 70453060, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,5-Dimethyl-3-(methoxycarbonyl)methylene-3,4,5,6-tetrahydro-1,4-oxazine-2-one was prepared as follows: 2-amino-2-methyl-1-propanol (5.35 ml, 0.056 mol) was dissolved in 100 ml of anhydrous ethanol. Dimethyl acetylenedicarboxylate (7.20 ml, 0.056 mol) was added dropwise at a rate which caused the solution to mildly reflux. Then, the reaction mixture was stirred at ambient temperature for 2 hours, and the solvent was evaporated to yield the desired 1,4-oxazinone derivative. After recrystallization from ethanol, 5.79 g of pure product was obtained melting at 94°-97° C.

Workup

  1. temperatureto mildly reflux
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-666ffb6511ee4a9fb0ea7582aab221af
Source dataset
uspto-grants-1985_10
Patent number
US04549014

Reaction notes

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