Dimethyl Sulfide → 2,4-Dimethyl-1,3-thiazole-5-carbaldehyde

Temperature

-78 °C

A 3-neck 100 mL round-bottom flask was charged with anhydrous CH2Cl2 (20 mL) and oxalyl chloride (1.0 mL, 11.25 mmol) under N2 atmosphere. The mixture was cooled to −78° C. Anhydrous DMS O (1.1 mL, 15 mmol) was slowly added. The reaction was allowed to stir for 30 min. 2,4-dimethylthiazole-5-methanol (1.181 g, 7.5 mmol) in CH2Cl2 (5 mL) was slowly added. The reaction was allowed to stir for about 3 h, until TLC (1:1 EtOAc/Hexane) showed no starting material. The reaction was quenched with triethylamine (4.3 mL, 30 mmol) and stirred for 10 min. before warming to room temperature. The reaction was poured into Et2O (100 mL) and then extracted with water (2×25 mL). The organic phase was washed with NaHCO3(aq) (25 mL) and brine (25 mL). Dry over MgSO4 and concentrated under vacuum. The product was stored in the freezer. Yield: 1.04 g (89%) orange crystalline solid.

1. stirringstirred for 10 min.
2. temperaturebefore warming to room temperature
3. extractionextracted with water (2×25 mL)
4. washThe organic phase was washed with NaHCO3(aq) (25 mL) and brine (25 mL)
5. dry with materialDry over MgSO4
6. concentrationconcentrated under vacuum

ORD record

ord-b498c2c635864fdab4d1af252ee5ecc9

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06204293B1