Benzene → HCID 20300005, compound

HRID 1733688Notes

Reaction equation

HRID 1733688 reaction equation
C1C=CC=CC=1.[OH:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=2[N:10]=[N:9]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(OCC)(=O)C.O>[CH3:25][S:26]([O:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=2[N:10]=[N:9]1)(=[O:28])=[O:27]

Participants

7

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 16765163HCID 16765163, compound

Product 1

HCID 20300005HCID 20300005, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To benzene (14 ml) are added 1-hydroxy-4-chloro-1,2,3-benzotriazole (3.4 g) and further triethylamine (2.8 ml). To the solution is added methanesulfonyl chloride (2.3 g) with stirring under ice-cooling and the mixture is stirred at the same temperature for 20 minutes and further at room temperature for 1.5 hours. After allowing to stand overnight, to the reaction mixture are added water (20 ml) and ethyl acetate (30 ml) and the ethyl acetate layer is separated. The water layer is again extracted with ethyl acetate (20 ml). The ethyl acetate extracts are combined, washed with a small amount of a saturated aqueous sodium hydrogen carbonate and water in order, dried over anhydrous sodium sulfate and the solvent is distilled off under a reduced pressure. The residue is washed with petroleum ether (10 ml) to give faint yellow crystals of 1-methanesulfonyloxy-4-chloro-1,2,3-benzotriazole (3.89 g; 79%), melting point: 71°-74° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the same temperature for 20 minutes and further at room temperature for 1.5 hours
  3. customthe ethyl acetate layer is separated
  4. extractionThe water layer is again extracted with ethyl acetate (20 ml)
  5. washwashed with a small amount of a saturated aqueous sodium hydrogen carbonate and water in order
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent is distilled off under a reduced pressure
  8. washThe residue is washed with petroleum ether (10 ml)

Sources & evidence

ORD record
ord-7ed8b64cc68340c59fb1663f08d33f05
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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