Chlorosulfamic acid → (E)-2-Sulfamoylamino-6-(prop-1-enyl)benzonitrile

A solution of (E)-2-amino-6-(prop-1-enyl)benzonitrile (Example 130b) (0.60 g, 3.82 mmol) in N,N-dimethylacetamide (DMA) (15.5 mL), under a nitrogen atmosphere, was treated with sulfamoyl chloride (0.88 g, 7.63 mmol) at room temperature. The obtained mixture was stirred at room temperature for 2 h and the reaction was quenched with water (20 mL). The mixture was extracted with EtOAc (4×80 mL), the combined extract was washed with water (2×20 mL) and brine, and dried with MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel using gradient hexanes to hexanes/EtOAc (1:1) to give 0.83 g (92%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 9.39 (broad s, 1H), 7.48-7.60 (m, 2H), 7.38-7.43 (m, 1H), 7.21 (broad s, 2H), 6.51-6.65 (m, 2H), 1.88-1.94 (m, 3H).

1. customthe reaction was quenched with water (20 mL)
2. extractionThe mixture was extracted with EtOAc (4×80 mL)
3. extractionthe combined extract
4. washwas washed with water (2×20 mL) and brine
5. dry with materialdried with MgSO4
6. customThe filtrate was evaporated
7. customthe residue was purified by chromatography on silica gel using gradient hexanes to hexanes/EtOAc (1:1)

ORD record

ord-2133e2b10d844bee8d018c7f047d4638

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181276B2