4-Methylmorpholine → 4-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonate

Participants

Reaction Steps

A solution of 3.11 g (27 mmole) of 5-(hydroxymethyl)thiazole and excess N-methyl morpholine in 100 ml of methylene chloride was cooled to 0° C. and treated with 8.2 g (41 mmole) of 4-nitrophenyl chloroformate. After being stirred for 1 h, the reaction mixture was diluted with CHCl3, washed successively with 1N HCI, saturated aqueous NaHCO3, and saturated brine, dried over NaSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (SiO2, 1-2% MeOH/CHCl3, Rf=0.5 in 4% MeOH/CHCl3) to provide the desired compound as a yellow solid. Yield: 5.9 g, 78%. The NMR and mass spectral data were identical to the ((5-thiazolyl)-methyl)-(4-nitrophenyl)carbonate product prepared in Example 7.

Provenance & Evidence