Hydrochloric Acid → [3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone

Temperature

0 °C

To a stirred solution of 1-methyl-1H-tetrazole (4.20 g, 50 mmol) in anhydrous THF (200 mL), cooled to 0° C. with a brine/ice bath, was added dropwise a solution of isopropylmagnesium chloride (2 M in THF, 30 mL, 60.2 mmol). After the addition was over, the resulting cloudy suspension was stirred for 15 min at 0° C. A solution of N-methoxy-N-methyl-3-(methylsulfanyl)benzamide (10.2 g, 39 mmol) in THF (80 mL) was then added dropwise while keeping the internal temperature below 5° C. The reaction mixture was then allowed to warm up and stirred overnight at room temperature. Aq. HCl (1 M, 65 mL) was added to the reaction mixture, the layers were separated, the water phase was extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried over MgSO4. Purification on silica gel afforded [3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone as a yellow solid [5.95 g, yield 43%; HPLC/MS: m/z=235 (M+H); logP(HCOOH)=2.52].

1. additionAfter the addition
2. customthe internal temperature below 5° C
3. temperatureto warm up
4. stirringstirred overnight at room temperature
5. customthe layers were separated
6. extractionthe water phase was extracted with ethyl acetate (3×50 mL)
7. dry with materialthe combined organic layers were dried over MgSO4
8. customPurification on silica gel

ORD record

ord-40431746223d4e5c84d0bbbccb48f7e1

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2