Dimethylthiocarbamoyl chloride → HCID 15077128, compound

To a mixture of 4-hydroxy-2-methyl-thiazole-5-carboxylic acid ethyl ester (7.2 g, 37.4 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (11.2 ml, 74.8 mmol) in DMF (50 ml) is added N,N-dimethyl-carbamothioyl chloride (6.94 g, 56.1 mmol). The mixture is stirred at RT for 14 h and at 60° C. for 3 h, poured onto water (100 ml) and extracted with EtOAc (3×50 ml). The combined organic layers are washed with water (2×50 ml), dried over sodium sulfate and concentrated. The residue is chromatographed (silica gel, 10% EtOAc/hexane) to give 4-(dimethyl-carbamothioyl)oxy-2-methyl-thiazole-5-carboxylic acid ethyl ester (5.7 g, 20.7 mmol, 55%).

1. additionpoured onto water (100 ml)
2. extractionextracted with EtOAc (3×50 ml)
3. washThe combined organic layers are washed with water (2×50 ml)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customThe residue is chromatographed (silica gel, 10% EtOAc/hexane)

ORD record

ord-e8b5fe843ae44d2c92c40aaef50f9787

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284286B2