Sulfamide → 3-[(sulfamoylamino)methyl]-1-benzothiophene

HRID 2061902Notes

Reaction equation

HRID 2061902 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].[BH4-].[Na+]>C(O)C.O>[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

6

Reactant 3

HCID 82267SulfamideHCID 2273281-Benzothiophene-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 116873763-[(sulfamoylamino)methyl]-1-benzothiophene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Thianaphthene-3-carboxaldehyde (1.62 g, 10.0 mmol) was dissolved in anhydrous ethanol (50 mL). Sulfamide (4.0 g, 42 mmol) was added and the mixture was heated to reflux for 16 hours. The mixture was cooled to room temperature. Sodium borohydride (0.416 g, 11.0 mmol) was added and the mixture was stirred at room temperature for three hours. The reaction was diluted with water (50 mL) and extracted with chloroform (3×75 mL). The extracts were concentrated and chromatographed (5% methanol in DCM) to yield the title compound as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 hours
  3. extractionextracted with chloroform (3×75 mL)
  4. concentrationThe extracts were concentrated
  5. customchromatographed (5% methanol in DCM)

Sources & evidence

ORD record
ord-451a831b76af4bf48f3bb01ac4799685
Source dataset
uspto-grants-2012_10
Patent number
US08283478B2

Reaction notes

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