Cyanamide → 2-Amino-4-undecyloxazole

HRID 373175Notes

Reaction equation

HRID 373175 reaction equation
[OH:1][CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[N:16]#[C:17][NH2:18].C([O-])(=O)C.[Na+]>C1COCC1.C(OCC)(=O)C.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[NH2:18][C:17]1[O: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][CH3:14])[N:16]=1

Participants

8

Reactant 3

HCID 9864CyanamideHCID 517045Sodium AcetateHCID 134236451-Hydroxytridecan-2-one

Product 1

HCID 198120172-Amino-4-undecyloxazoleYield 63%

Reagents, catalysts & solvents 4

HCID 14798Sodium HydroxideCatalystHCID 2723671Tetrabutylammonium HydroxideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-hydroxy-2-tridecanone (1.0 g, 4.7 mmol) and cyanamide (0.2 g, 5 mmol) in THF (3.0 mL) was added aqueous sodium acetate (2.0 mL, 1.0 N), tetra n-butylammoniumhydroxide (0.6 mL, 0.4 N 0.2 mmol), and sodium hydroxide (0.2 mL, 1.0 N, 0.2 mmol) sequentially. The resulting two-phase mixture was stirred (48 hours, 25° C.). The resulting mixture was taken up in ethyl acetate (200 mL), washed with brine (2×65 mL), dried (MgSO4), and concentrated in vacuo. The residue was chromatographed on silica (pure chloroform to 95:5 chloroform:methanol) and concentrated in vacuo to yield 0.70 g (63%) of the title compound as an off-white powder, m.p. 55°-58° C.

Workup

  1. washwashed with brine (2×65 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica (pure chloroform to 95:5 chloroform:methanol)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-599813f4c47f4e13b890e3f6a9eccd9e
Source dataset
uspto-grants-1992_11
Patent number
US05162360

Reaction notes

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