Water → 2'-Nitrobiphenyl-4-yl sulfamate

HRID 1883660Notes

Reaction equation

HRID 1883660 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([O-:3])=[O:2].[H-].[Na+].[S:19](Cl)(=[O:22])(=[O:21])[NH2:20].O>CN(C)C=O>[S:19](=[O:22])(=[O:21])([O:16][C:13]1[CH:12]=[CH:11][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)[NH2:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 155411124-Hydroxy-2'-nitrobiphenyl

Product 1

HCID 99041872'-Nitrobiphenyl-4-yl sulfamateYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

108 mg of 2′-nitrobiphenyl-4-ol was dissolved in 1.5 ml of N,N-dimethyformamide, and a suspension of 120 mg of sodium hydride in 1.5 ml of N,N-dimethyformamide was added thereto under cooling with ice, followed by stirring for 10 minutes under cooling with ice. 367 mg of sulfamoyl chloride was added to this mixture, followed by stirring at room temperature for 3 hours. After water was added to the reaction mixture, 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 1:1 mixture of ethyl acetate and hexane as the developing solvent) to obtain 106 mg of 2′-nitrobiphenyl-4-yl sulfamate.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. stirringby stirring at room temperature for 3 hours
  5. extractionthe product was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium
  8. distillationAfter the solvent was distilled off
  9. customthe resulting crude product was purified by TLC (
  10. additiona 1:1 mixture of ethyl acetate and hexane as the developing solvent)

Sources & evidence

ORD record
ord-2e704ae4ed14478688fb927a2c15fb97
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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