Maximum quantity allowed is 999
Please select the quantity
TCI Practical Example: Synthesis of a Carbamate Using DPPA
We are proud to present the synthesis of the carbamate via the Curtius rearrangement using thiazole-4-carboxylic acid, DPPA and tert-butyl alcohol.
Used Chemicals
Procedure
DPPA (0.92 mL, 4.26 mmol, 1.1 equiv.) was added to a solution of thiazole-4-carboxylic acid (500 mg, 3.87 mmmol) and triethylamine (0.59 mL, 4.26 mmol, 1.1 equiv.) in tert-butyl alcohol (2 mL) at 0 °C and the solution was stirred for 30 minutes. Then, the reaction mixture was heated to 90 °C and stirred for 21 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate:hexane = 0:1 - 1:1 on silica gel) to give tert-butyl N-thiazol-4-ylcarbamate as a white solid (591 mg, 76% yield).
Experimenter's Comments
The reaction mixture was monitored by HPLC.
TLC analysis of the target product showed Rf = 0.4 (ethyl acetate:hexane = 1:4).
Analytical Data
tert-Butyl N-Thiazol-4-ylcarbamate
1H NMR (270 MHz, CDCl3); δ 8.58 (d, J = 2.2 Hz, 1H), 8.06 (brs, 1H), 7.29 (brs, 1H), 1.51 (s, 9H).
Lead Reference
- Novel Syntheses of Variably Substituted Pyrrolo[2,3-d]thiazoles
