Water → HCID 13145832, compound

HRID 1733705Notes

Reaction equation

HRID 1733705 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>C1C=CC=CC=1>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:1][N:2]2[C:6]3[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=3[N:4]=[N:3]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2327116-Chloro-1-hydroxy-1H-benzotriazole

Product 1

HCID 13145832HCID 13145832, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In dry benzene (50 ml) are dissolved 1-hydroxy-6-chloro-1,2,3-benzotriazole (8.5 g) and triethylamine (7.0 ml), and thereto is added p-toluenesulfonyl chloride (9.5 g) at room temperature and the mixture is stirred for 1 hour. To the reaction mixture are added water and benzene. The benzene layer is separated, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The resulting residue is recrystallized from carbon tetrachloride to give 1-(p-toluenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (12.6 g), melting point: 94°-96° C.

Workup

  1. customThe benzene layer is separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe resulting residue is recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-9e8583820e5547f2aeed1dc497cd0e8f
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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