Triethylamine → 1-Methanesulfonyloxy-6-vinyl-1,2,3-benzotriazole
Reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([CH:11]=[CH2:12])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)(Cl)Cl>[CH3:20][S:21]([O:1][N:2]1[C:6]2[CH:7]=[C:8]([CH:11]=[CH2:12])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1)(=[O:23])=[O:22]Participants
Procedure
In chloroform (80 ml) are dissolved 1-hydroxy-6-vinyl-1,2,3-benzotriazole (8.0 g) and triethylamine (5.1 g) under stirring, and thereto is added dropwise a solution of methanesulfonyl chloride (5.73 g) in chloroform (20 ml) at a temperature of less than 10° C. The mixture is stirred at room temperature for 1.5 hours. The reaction mixture is washed with water, an aqueous sodium hydrogen carbonate and water in order, dried over anhydrous magnesium sulfate, treated with charcoal and then concentrated till about 40 ml. After dissolving the precipitated crystals by heating, the mixture is allowed to stand. The precipitated crystals are separated by filtration to give 1-methanesulfonyloxy-6-vinyl-1,2,3-benzotriazole (9.1 g), melting point: 129°-129.5° C. The filtrate is concentrated, and the resulting residue is recrystallized from benzene to give additionally the desired product (2.3 g).
Workup
- stirringThe mixture is stirred at room temperature for 1.5 hours
- washThe reaction mixture is washed with water
- dry with materialan aqueous sodium hydrogen carbonate and water in order, dried over anhydrous magnesium sulfate
- additiontreated with charcoal
- concentrationconcentrated till about 40 ml
- dissolutionAfter dissolving the precipitated crystals
- temperatureby heating
- customThe precipitated crystals are separated by filtration
Sources & evidence
- ORD record
- ord-72c3c92554d94760907c5674da0dee6b
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04242507
Reaction notes
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