Water → HCID 86584208, compound

HRID 1837412Notes

Reaction equation

HRID 1837412 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([CH2:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])(=[O:13])=[O:12].S([N:32]=[N+:33]=[N-])(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C.O>C(#N)C.ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:14]([S:15]([C:18]([F:21])([F:19])[F:20])(=[O:16])=[O:17])=[N+:32]=[N-:33])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 22677136HCID 22677136, compound

Product 1

HCID 86584208HCID 86584208, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Crude 2-naphthalenesulfonyl-trifluoromethanesulfonyl-methane (5 g, 0.014 mole) is dissolved in acetonitrile (150 ml) under nitrogen and the solution is cooled to 0° C. using an ice bath. Tosyl azide (8.3 g, 0.042 mole) and then triethylamine (3.9 ml, 0.028 mole) are added in one portion and the reaction mixture is stirred at that temperature for 24 h. After adding water (400 ml) and dichloromethane (200 ml), the phases are separated and the aqueous layer is extracted twice with dichloromethane (150 ml) and the combined organic phases are washed with 1 N HCl, saturated sodium bicarbonate and water. After drying over MgSO4 and removal of the solvent, the crude product is obtained as orange oil.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous layer is extracted twice with dichloromethane (150 ml)
  3. washthe combined organic phases are washed with 1 N HCl, saturated sodium bicarbonate and water
  4. dry with materialAfter drying over MgSO4 and removal of the solvent

Sources & evidence

ORD record
ord-8f1beb0aaa4f444c93b16c30dd22cacb
Source dataset
uspto-grants-2004_08
Patent number
US06783912B2

Reaction notes

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