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

HRID 1939866Notes

Reaction equation

HRID 1939866 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 hour, 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-1.

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-fe6c57e8d4ff4a4da1d0e8a4b20cfdba
Source dataset
uspto-grants-1997_12
Patent number
US05698526

Reaction notes

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