Triethylamine → HCID 20300022, compound

HRID 1733710Notes

Reaction equation

HRID 1733710 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.C(N(CC)CC)C.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[S:27]([O:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1)(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 20300022HCID 20300022, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (70 ml) are added 1-hydroxy-1,2,3-benzotriazole (3.4 g) and further triethylamine (3.7 ml). To the solution is added dropwise a solution of 2,4,6-trimethylbenzenesulfonyl chloride (4.5 g) is dichloromethane (20 ml) at room temperature, and the mixture is stirred for 1 hour. The reaction mixture is washed with water and dried over anhydrous magnesium sulfate, and the solvent is distilled off. The resulting residue is washed with ethyl acetate-n-hexane (1:1; 50 ml) and dried to give colorless crystals of 1-(2,4,6-trimethylbenzenesulfonyloxy)-1,2,3-benzotriazole (5.5 g), melting point: 128°-130° C. The product is recrystallized from dichloromethane-n-hexane to give colorless prisms, melting point: 130°-131° C.

Workup

  1. customat room temperature
  2. washThe reaction mixture is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off
  5. washThe resulting residue is washed with ethyl acetate-n-hexane (1:1; 50 ml)
  6. customdried

Sources & evidence

ORD record
ord-cf986494ebd940faacf810ab76d16980
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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