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

HRID 2061913Notes

Reaction equation

[CH:1]1[CH:6]=[C:5]2[C:7]([CH:10]=O)=[CH:8][S:9][C:4]2=[CH:3][CH:2]=1.[S:12]([NH2:16])([NH2:15])(=[O:14])=[O:13].S(=O)(=O)(O)N.[BH4-].[Na+].Cl>C(O)C>[S:9]1[CH:8]=[C:7]([CH2:10][NH:15][S:12]([NH2:16])(=[O:14])=[O:13])[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]1=2

Participants

Conditions

Temperature: 45 °C

Procedure

Thianaphthene-3-carboxaldehyde (5 g, 30.8 mmol) was dissolved in anhydrous ethanol (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. Sodium borohydride (1.2 g, 30.8 mmol) was added and the reaction mixture was stirred for 1 hour. 1N HCl (30 mL, 30 mmol) was added and the reaction mixture was filtered through Celite. The filtered solution was then diluted with water (100 mL). The precipitate was filtered to yield the title compound as a off white solid.

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationthe reaction mixture was filtered through Celite
additionThe filtered solution was then diluted with water (100 mL)
filtrationThe precipitate was filtered

Sources & evidence

ORD record: ord-66b4b7554a1c4be28ed497df2d21f345
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283478B2

Reaction notes

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