Phosgene → HCID 86622753, compound

Participants

Reaction Conditions

Reaction Steps

Phosgene (54.0 mmol, 27.9 mL of a 1.93 M solution in toluene) was placed in a 3-neck-flask and cooled to 0° C. THF (10 mL) was added, followed by a mixture of piperonylamine (27.0 mmol, 4.0 g) and DIPEA (56.7 mmol, 7.3 g) in THF (20 mL) at 0° C. After complete addition the mixture was stirred for another 40 min at 0° C. The reaction mixture was then concentrated. To the crude material THF (40 mL) and DIPEA (4.4 mL) were added. This mixture was then added to a slurry of 2-amino-4-(chloromethyl)thiazole hydrochloride (24.3 mmol, 4.5 g) in THF (50 mL). After stirring for 72 h at room temperature the reaction mixture was filtered through celite. The celite was washed with ethylacetate. The combined filtrate was concentrated and the material was directly applied to column chromatography (MeOH/DCM) providing 2.6 g (32%) of the desired intermediate. 1H-NMR (CD3OD, 300 MHz) δ 6.96 (s, 1H), 6.79 (m, 3H), 5.91 (s, 2H), 4.55 (s, 2H), 4.32 (s, 2H).

Provenance & Evidence