Triethylamine → 1-(4-Methylthiazol-2-ylsulfonyloxy)-1,2,3-benzotriazole

HRID 1768389Notes

Reaction equation

HRID 1768389 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([S:7](Cl)(=[O:9])=[O:8])[S:5][CH:6]=1.[OH:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[N:13]1.C(N(CC)CC)C.C(OCC)(=O)C>C(OC)(C)(C)C>[CH3:1][C:2]1[N:3]=[C:4]([S:7]([O:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[N:13]2)(=[O:9])=[O:8])[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 116800074-methyl-1,3-thiazole-2-sulfonyl Chloride

Product 1

HCID 178646141-(4-Methylthiazol-2-ylsulfonyloxy)-1,2,3-benzotriazole

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Under atmosphere of argon, to a solution of 4-methylthiazol-2-sulfonyl chloride in methyl t-butyl ether (0.20 M, 20 ml), 1-hydroxybenzotriazole (549 mg) and triethylamine (0.57 ml) were added under stirring with cooled on ice bath, and the mixture was stirred for 1 hour at room temperature. To the reaction mixture, ethyl acetate was added. The organic layer was washed with water three times, with a saturated aqueous solution of sodium chloride once successively, dried over an anhydrous magnesium sulfate and concentrated to give the compound of the present invention (1.1 g) having the following physical data. NMR: δ 8.03 (dt, J=8.4, 1.0 Hz, 1H), 7.70-6.57 (m, 2H), 7.53 (d, J=1.0 Hz, 1H), 7.46 (ddd, J=8.4, 5.8, 2.0 Hz, 1H), 2.62 (d, J=1.0 Hz, 3H).

Workup

  1. temperaturewith cooled on ice bath
  2. stirringthe mixture was stirred for 1 hour at room temperature
  3. washThe organic layer was washed with water three times, with a saturated aqueous solution of sodium chloride once successively
  4. dry with materialdried over an anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give the compound of the present invention (1.1 g)

Sources & evidence

ORD record
ord-6b75d4293ee343f581dd46eaa9460551
Source dataset
uspto-grants-2007_06
Patent number
US07235667B2

Reaction notes

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