2-phenoxyethanethioamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-bromodihydro-1-[(4-methoxyphenyl)methyl]-1H-azepine-2,4(3H,5H)-dione (0.78 g, 2.38 mmol) and 2-phenoxythioacetamide (0.36 g, 2.14 mmol) in DMF (12.5 mL) was stirred at room temperature for 15 minutes. Then NaHCO3 (0.32 g, 3.81 mmol) was added and the reaction was stirred at 100° C. for 30 minutes. The reaction was diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM in Heptane 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 5,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.58 g, 62% yield) as an orange oil. C22H22N2O3S LCMS: Rt 3.01, m/z 395 [M+H]+ (using method, LC-MS Method 6). the reaction was stirred at 100° C. for 30 minutes extracted with AcOEt The organic layer was separated dried (Na2SO4) filtered the solvents evaporated in vacuo The crude product was purified by flash column chromatography (silica; DCM in Heptane 0/100 to 100/0) The desired fractions were collected the solvents evaporated in vacuo