Chlorosulfamic acid → (E)-2-sulfamoylamino-6-(3-methoxyprop-1-enyl)benzonitrile

HRID 711703Notes

Reaction equation

HRID 711703 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](/[CH:10]=[CH:11]/[CH2:12][O:13][CH3:14])[C:3]=1[C:4]#[N:5].[NH2:15][S:16](Cl)(=[O:18])=[O:17]>CC(N(C)C)=O.CCOC(C)=O>[S:16]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](/[CH:10]=[CH:11]/[CH2:12][O:13][CH3:14])[C:3]=1[C:4]#[N:5])(=[O:18])(=[O:17])[NH2:15]

Participants

5

Reactant 2

HCID 24499Chlorosulfamic acidHCID 67399559(E)-2-amino-6-(3-methoxyprop-1-enyl)benzonitrile

Product 1

HCID 67399392(E)-2-sulfamoylamino-6-(3-methoxyprop-1-enyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of (E)-2-amino-6-(3-methoxyprop-1-enyl)benzonitrile (Example 97b) (188 mg, 1.0 mmol) in DMA was added NH2SO2Cl (347 mg, 3.0 mmol) at 0° C. under nitrogen. The reaction mixture was then stirred at room temperature for 6 hrs, diluted with EtOAc, washed with brine (5×), and dried over Na2SO4. The solvent was evaporated under reduced pressure to give (E)-2-sulfamoylamino-6-(3-methoxyprop-1-enyl)benzonitrile as a pale-yellow solid, which was used in the next step without further purification.

Workup

  1. washwashed with brine (5×)
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b4092b443d554c08bc83dd5dd4795ef5
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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