Water → 2'-Nitrobiphenyl-4-yl sulfamate

HRID 1883661Notes

Reaction equation

HRID 1883661 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].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.[S:32](Cl)(=[O:35])(=[O:34])[NH2:33].O>C(Cl)Cl>[S:32](=[O:35])(=[O:34])([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)[NH2:33]

Participants

6

Reactant 4

HCID 962WaterHCID 24499Chlorosulfamic acidHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 155411124-Hydroxy-2'-nitrobiphenyl

Product 1

HCID 99041872'-Nitrobiphenyl-4-yl sulfamateYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

108 mg of 2′-nitrobiphenyl-4-ol was dissolved in 9.5 ml of methylene chloride, and 312 mg of 2,6-di-tert-butyl-4-methylpyridine and 347 mg of sulfamoyl chloride were successively added thereto under cooling with ice, followed by stirring at room temperature for 5 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 149 mg of 2′-nitrobiphenyl-4-yl sulfamate.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe resulting crude product was purified by TLC (
  7. additiona 1:1 mixture of ethyl acetate and hexane as the developing solvent)

Sources & evidence

ORD record
ord-08abfe412c9a4c429c4a6c61217c911b
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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