Sulfamide → 2-Sulfamoylamino-6-(3-(trimethylsilyl)prop-1-ynyl)benzonitrile

HRID 471752Notes

Reaction equation

HRID 471752 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[C:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:3]=1[C:4]#[N:5].[NH2:17][S:18](N)(=[O:20])=[O:19]>O1CCOCC1>[S:18]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]#[C:11][CH2:12][Si:13]([CH3:14])([CH3:16])[CH3:15])[C:3]=1[C:4]#[N:5])(=[O:20])(=[O:19])[NH2:17]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 674002162-Amino-6-(3-(trimethylsilyl)prop-1-ynyl)benzonitrile

Product 1

HCID 674011982-Sulfamoylamino-6-(3-(trimethylsilyl)prop-1-ynyl)benzonitrileYield 5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-6-(3-(trimethylsilyl)prop-1-ynyl)benzonitrile (Example 253b) (557 mg, 2.0 mmol) and NH2SO2NH2 (0.96 g, 10 mmol) in dry 1,4-dioxane (50 mL) was refluxed under nitrogen for 2 days. The solvent was evaporated under reduced pressure, and the residue was purified by chromatography on silica gel eluting with 70% EtOAc in hexanes to give the title compound (31 mg, 5%) as a white solid. MS 308 (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel eluting with 70% EtOAc in hexanes

Sources & evidence

ORD record
ord-c60470cedb024c8f80a43eafc2d41869
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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