Sulfamide → HCID 11499667, compound

HRID 2061903Notes

Reaction equation

HRID 2061903 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3]1.[S:13]([NH2:17])([NH2:16])(=[O:15])=[O:14].[BH4-].[Na+]>C(O)C.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:16][S:13]([NH2:17])(=[O:15])=[O:14])=[CH:3]1

Participants

6

Reactant 3

HCID 82267Sulfamide2×HCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 11499667HCID 11499667, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-Methylindole-3-carboxaldehyde (1.66 g, 10.4 mmol) was dissolved in anhydrous ethanol (50 mL). Sulfamide (4.5 g, 47 mmol) was added and the mixture was heated to reflux for 16 hours. Additional sulfamide (1.0 g, 10.4 mmol) was added and the mixture was heated to reflux for 24 hours. The mixture was cooled to room temperature. Sodium borohydride (0.722 g, 12.5 mmol) was added and the mixture was stirred at room temperature for one hour. The reaction was diluted with water (50 mL) and extracted with DCM (3×75 mL). The extracts were concentrated and about 1 mL of methanol was added to create a slurry which was filtered to yield the title compound as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 hours
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 24 hours
  5. extractionextracted with DCM (3×75 mL)
  6. concentrationThe extracts were concentrated
  7. additionabout 1 mL of methanol was added
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-74c281b934cd4a0bb499bc5c6a3aee53
Source dataset
uspto-grants-2012_10
Patent number
US08283478B2

Reaction notes

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