Sodium Hydroxide → 3-Amino-5-dodecylisoxazole

HRID 373170Notes

Reaction equation

HRID 373170 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[CH: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])[O:19][N:18]=1

Participants

5

Reactant 3

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

Product 1

HCID 198120213-Amino-5-dodecylisoxazoleYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2 -pentadecynenitrile (2.9 g, 13.2 mmol) in ethanol (60 mL) was added to a stirred solution of hydroxylamine hydrochloride (1.1 g, 15.8 mmol) in 1.0 N NaOH (29.1 mL, 29.1 mmol). The resulting mixture was stirred for 16 hours (25° C.). The resulting slurry was filtered and the crystals were washed with cold water and dried in a vacuum oven at 40° C. (24 hours) to yield 2.4 g (71.9%) of 3-amino-5-dodecyl-isoxazole as white platelets; m.p. 79.5°-81° C.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washthe crystals were washed with cold water
  3. customdried in a vacuum oven at 40° C. (24 hours)

Sources & evidence

ORD record
ord-e9759849044c41f8988cf800d3df99d7
Source dataset
uspto-grants-1992_11
Patent number
US05162360

Reaction notes

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