HCID 12125209, compound → HCID 23508408, compound

HRID 1883666Notes

Reaction equation

HRID 1883666 reaction equation
[S:1](=[O:22])(=[O:21])([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2[C:19]#[N:20])=[CH:6][CH:5]=1)[NH2:2]>C(O)=O.[C].[Pd]>[S:1](=[O:21])(=[O:22])([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=2[C:19]#[N:20])=[CH:8][CH:9]=1)[NH2:2]

Participants

4

Reactant 1

HCID 12125209HCID 12125209, compound

Product 1

HCID 23508408HCID 23508408, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 284Formic AcidSolvent

Procedure

262 mg of 2′-cyano-4′-nitrobiphenyl-4-yl sulfamate was dissolved in 2.5 ml of formic acid, and 445 mg of 10% palladium-carbon was added thereto, followed by stirring at room temperature for 5 minutes. After the reaction mixture was filtered to remove any insoluble matter and the filtrate was poured into a saturated aqueous solution of sodium chloride, the product was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the resulting crude product was purified by TLC (using a 10:1 mixture of chloroform and methanol as the developing solvent) to obtain 52 mg of 4′-amino-2′-cyanobiphenyl-4-yl sulfamate.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. customto remove any insoluble matter
  3. additionthe filtrate was poured into a saturated aqueous solution of sodium chloride
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe resulting crude product was purified by TLC (
  9. additiona 10:1 mixture of chloroform and methanol as the developing solvent)

Sources & evidence

ORD record
ord-5543d7fc4c5b4cdeacbf1899a95fcbc9
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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