Water → HCID 20300016, compound

HRID 1733686Notes

Reaction equation

HRID 1733686 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(OCC)(=O)C.O>[OH-].[Na+]>[CH3:14][S:15]([O:1][N:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 31297Methanesulfonyl chlorideHCID 1528171-Hydroxy-6-nitrobenzotriazole

Product 1

HCID 20300016HCID 20300016, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1-Hydroxy-6-nitro-1,2,3-benzotriazole (7.2 g) is dissolved in 1 N aqueous sodium hydroxide (40 ml). To the solution is added dropwise methanesulfonyl chloride (5.6 g) with stirring under ice-cooling and thereto are added ethyl acetate (100 ml) and water (100 ml). The mixture is stirred at room temperature for 1 hour. To the reaction mixture is added ethyl acetate (50 ml) and the insoluble materials are filtered off. The ethyl acetate layer is dried over magnesium sulfate-charcoal. After drying, the layer is concentrated so as to be about 30 ml and thereto is added n-hexane (about 30 ml) and the mixture is allowed to stand. The precipitated crystals are separated by filtration and dried to give 1-methanesulfonyloxy-6-nitro-1,2,3-benzotriazole (7.3 g; 72%), melting point: 115°-116° c. The product is dissolved in ethyl acetate and treated with charcoal and thereto is added n-hexane to give faint yellow flakes melting point: 117°-118° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. filtrationthe insoluble materials are filtered off
  4. dry with materialThe ethyl acetate layer is dried over magnesium sulfate-charcoal
  5. customAfter drying
  6. concentrationthe layer is concentrated so as
  7. additionis added n-hexane (about 30 ml)
  8. customThe precipitated crystals are separated by filtration
  9. customdried

Sources & evidence

ORD record
ord-62a2396a0b7140f4a3d6aa6f112f588b
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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