Chlorosulfamic acid → HCID 67397635, compound

HRID 471573Notes

Reaction equation

HRID 471573 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]#[N:8].[S:9](Cl)(=[O:12])(=[O:11])[NH2:10]>CC(N(C)C)=O.CCOC(C)=O>[S:9]([NH:1][C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[C:7]#[N:8])(=[O:12])(=[O:11])[NH2:10]

Participants

5

Reactant 2

HCID 24499Chlorosulfamic acidHCID 2872752-Aminocyclopent-1-ene-1-carbonitrile

Product 1

HCID 67397635HCID 67397635, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-aminocyclopent-1-enecarbonitrile (440 mg, 4.07 mmol) in 10 mL of DMA was added sulfamoyl chloride (941.3 mg, 8.15 mmol), and the resultant mixture was stirred at room temperature under nitrogen for 2 h. Then it was diluted with EtOAc, the organic layer was washed with brine and dried down under vacuum, and the residue was purified by chromatography on silica gel eluting with EtOAc/Hexane to give the title compound. 1H NMR (400 MHz, CDCl3) δ 2.04-1.97 (m, 2H), 2.61-2.57 (m, 2H), 2.9-2.86 (m, 2H), 5.66 (s, 2H), 8.04 (s, 1H).

Workup

  1. washthe organic layer was washed with brine
  2. customdried down under vacuum
  3. customthe residue was purified by chromatography on silica gel eluting with EtOAc/Hexane

Sources & evidence

ORD record
ord-34dcd856750a48a5bf6c9d021b341f9b
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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