Dimethylformamide → HCID 67273752, compound

Temperature

80 °C

To a mixture of 0.368 g of the complex of sulfur trioxide with dimethylformamide in 1.5 ml dichloromethane was added 0.309 g 2-isobutyl-3-methyl-thiophene and the mixture was heated to 55° C. for 30 min. and to 80° C. for an other 30 min. The mixture was cooled to room temperature and 0.286 g thionylchloride was added. The mixture was heated to 55° C. for ca 30 min cooled to room temperature and poored onto ice and extracted with ethyl acetate, the phases were separated and the organic phase was washed with water and brine and evaporated. The residue was taken up in 10 ml acetone and mixed with 1 ml 25% aqueous ammonia for ca 30 min. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with ethyl acetate:heptane=1:3 to yield 0.16 g of the title compound as oil. MS (ISN) M−H+=232.0

1. temperatureThe mixture was cooled to room temperature
2. temperatureThe mixture was heated to 55° C. for ca 30 min
3. temperaturecooled to room temperature and poored onto ice
4. extractionextracted with ethyl acetate
5. customthe phases were separated
6. washthe organic phase was washed with water and brine
7. customevaporated
8. additionmixed with 1 ml 25% aqueous ammonia for ca 30 min
9. customThe reaction mixture was partitioned between water and ethyl acetate
10. customThe phases were separated
11. customthe organic phase was purified by chromatography on silica gel with ethyl acetate

ORD record

ord-86fe7fe0b98c49f6b21c34fa85a6dbcc

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163778B2