Sodium Hydroxide → 5-Amino-3-dodecylisoxazole

HRID 373168Notes

Reaction equation

HRID 373168 reaction equation
[C:1](#[N:16])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].Cl.[NH2:18][OH:19].[OH-].[Na+]>C(O)C>[NH2:16][C:1]1[O:19][N:18]=[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19812014HCID 19812014, compound

Product 1

HCID 198120305-Amino-3-dodecylisoxazoleYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 2-pentadecynenitrile (10.0 g, 45.6 mmol) in ethanol (50 mL) was added to a stirred solution of hydroxylamine hydrochloride (3.8 g, 54.6 mmol) in 2.5 N NaOH (20.0 mL, 50.1 mmol). The resulting mixture was diluted with ethanol (100 mL) and stirred (22 hours, 25° C.). The obtained slurry was concentrated, then partitioned between ethyl acetate (300 mL) and brine (100 mL). The organic layer was dried (MgSO4), concentrated in vacuo, and chromatographed on silica (95:5 to 70:30 hexane:ethyl acetate) to yield 8.2 g (71.2%) of 5-amino-3-dodecyl-isoxazole as a waxy solid, m.p. 48.5°-49.5° C.

Workup

  1. concentrationThe obtained slurry was concentrated
  2. custompartitioned between ethyl acetate (300 mL) and brine (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica (95:5 to 70:30 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2b18155a17f040288718388496505f35
Source dataset
uspto-grants-1992_11
Patent number
US05162360

Reaction notes

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