Hydrochloric Acid → 3-[(sulfamoylamino)methyl]-1-benzothiophene

Temperature

45 °C

Thianaphthene-3-carboxaldehyde (5 g, 30.8 mmol) was dissolved in THF (50 mL). Sulfamide (12.22 g, 123.30 mmoles) and sulfamic acid (0.29 g, 3.08 mmoles) were added and the reaction mixture heated to 45° C. for 18 h. The reaction mixture was then cooled to room temperature and filtered through a sintered glass funnel. The resulting solution was treated with lithium borohydride (2.0 M in THF, 5 mL, 10 mmol) via addition funnel. After addition (5 minutes) the reaction mixture was stirred for 1 hour. 1N HCl (20 mL, 20 mmol) was added and the reaction mixture concentrated to remove THF. The resulting suspension was treated with water (100 mL) and vigorously stirred. The resulting solid was filtered and dried to yield the title compound as a light pink solid.

1. temperatureThe reaction mixture was then cooled to room temperature
2. filtrationfiltered through a sintered glass funnel
3. additionAfter addition (5 minutes) the reaction mixture
4. concentrationthe reaction mixture concentrated
5. customto remove THF
6. additionThe resulting suspension was treated with water (100 mL)
7. stirringvigorously stirred
8. filtrationThe resulting solid was filtered
9. customdried

ORD record

ord-094c2ccc1d7f4316b81aac5dcb21e71e

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08283478B2