Toluene → 2'-Nitrobiphenyl-4-yl sulfamate

HRID 1883663Notes

Reaction equation

HRID 1883663 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].C1(C)C=CC=CC=1.Cl[S:25]([N:28]=C=O)(=[O:27])=[O:26]>O>[S:25](=[O:27])(=[O:26])([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)[NH2:28]

Participants

5

Reactant 3

HCID 1140TolueneHCID 70918Chlorosulfonyl isocyanateHCID 155411124-Hydroxy-2'-nitrobiphenyl

Product 1

HCID 99041872'-Nitrobiphenyl-4-yl sulfamateYield 54.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture composed of 215 mg of 2′-nitrobiphenyl-4-ol and 1 ml of toluene was cooled with ice, and 148 mg of chlorosulfonyl isocyanate was added dropwise thereto, followed by refluxing for 17 hours. After water was added to the reaction mixture under cooling with ice, 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 160 mg of 2′-nitrobiphenyl-4-yl sulfamate.

Workup

  1. additionwas added dropwise
  2. temperatureby refluxing for 17 hours
  3. temperatureunder cooling with ice
  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-c6814b83700a47f8a290bf46f634f0fb
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

Loading…