Benzene → HCID 20300045, compound

HRID 1733689Notes

Reaction equation

HRID 1733689 reaction equation
C1C=CC=CC=1.[OH:7][N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][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]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1)(=[O:28])=[O:27]

Participants

7

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2327116-Chloro-1-hydroxy-1H-benzotriazole

Product 1

HCID 20300045HCID 20300045, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into benzene (14 ml) is suspended 1-hydroxy-6-chloro-1,2,3-benzotriazole (3.4 g) and thereto is added 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 5 hours. 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 and dried over anhydrous sodium sulfate. After drying, the solvent is distilled off under a reduced pressure, and the residue is washed with petroleum ether (10 ml) to give colorless crystals of 1-methanesulfonyloxy-6-chloro-1,2,3-benzotriazole (1.55 g), melting point: 174°-175° C. (decomp). The remaining water layer after extracted with ethyl acetate, wherein precipitates are observed, is regulated at pH 1 with concentrated hydrochloric acid. The precipitates are separated by filtration and washed with water to give the desired product (2.4 g) as colorless crystals, melting point: 157°-158° C. (decomp).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at the same temperature for 20 minutes and further at room temperature for 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. customAfter drying
  8. distillationthe solvent is distilled off under a reduced pressure
  9. washthe residue is washed with petroleum ether (10 ml)

Sources & evidence

ORD record
ord-912a2a4bd1924c5486818a8b5aa43430
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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