1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(Azidomethyl)-1,3-thiazole

HRID 1585534Notes

Reaction equation

HRID 1585534 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[S:29]1[CH:33]=[CH:32][N:31]=[C:30]1[CH2:34]O>C1(C)C=CC=CC=1>[N:15]([CH2:34][C:30]1[S:29][CH:33]=[CH:32][N:31]=1)=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 27952131,3-Thiazol-2-ylmethanol

Product 1

HCID 212185832-(Azidomethyl)-1,3-thiazoleYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Diphenylphosphoryl azide (3.25 mL, 0.015 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.25 mL, 0.025 mol) were added to a solution of thiazol-2-yl-methanol (1.44 g, 0.013 mol) in toluene (20 mL) at 0° C. After 1 h the reaction was warmed to room temperature and stirred overnight. The mixture was diluted with toluene (20 mL) and washed with H2O (3×) brine (1×), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (30% ethyl acetate/hexanes) to afford the azide as a tan oil (1.1 g, 63%). IR 2098 cm. 1H NMR (250 MHz, CDCl3) δ 7.8 (d, 1H, J=2.0 Hz); 7.4 (d, 1H, J=2.0 Hz); 4.7 (s, 2H).

Workup

  1. washwashed with H2O (3×) brine (1×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cd28376cd05a494893e865600e5b09df
Source dataset
uspto-grants-1999_08
Patent number
US05939398

Reaction notes

Loading…