Sulfamide → HCID 67400064, compound

HRID 711701Notes

Reaction equation

HRID 711701 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[S:11](N)([NH2:14])(=[O:13])=[O:12]>O1CCOCC1>[S:11]([NH:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8])(=[O:13])(=[O:12])[NH2:14]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 2902362-Amino-4,5-dimethyl-thiophene-3-carbonitrile

Product 1

HCID 67400064HCID 67400064, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (Example 4b) (1.0 g, 6.57 mmol) in 1,4-dioxane (50 mL) was added sulfamide (3.87 g, 40.30 mmol). The reaction mixture was heated to reflux for 24 hr, after cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel eluting with EtOAc/Hexanes (2:3) to give 300 mg of product as a dark red oil. 1H NMR (400 MHz, DMSO-d6) δ 2.09 (3, 3H), 2.26 (s, 3H), 7.32 (s, 2H), 10.17 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hr
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by chromatography on silica gel eluting with EtOAc/Hexanes (2:3)

Sources & evidence

ORD record
ord-a5af030b32be4f66b1edcf862cd208e9
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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