4-Toluenesulfonyl chloride → HCID 11379486, compound

HRID 505005Notes

Reaction equation

HRID 505005 reaction equation
Br[CH2:2][CH2:3][OH:4].[N-:5]=[N+:6]=[N-:7].[Na+].[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>O>[C:15]1([CH3:16])[CH:17]=[CH:18][C:12]([S:9]([O:4][CH2:3][CH2:2][N:5]=[N+:6]=[N-:7])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 108982-BromoethanolHCID 33557Sodium Azide

Product 1

HCID 11379486HCID 11379486, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2-bromoethanol (5.06 g; 40.4 mmol) and sodium azide (3.12 g; 48 mmol; 1.2 equiv) in water (15 ml) is stirred at 60° C. for 4 hours, extracted with dichloromethane (4×20 ml), dried over sodium sulphate, filtered and concentrated (it should be noted that 2-azidoethanol is too volatile to be dried under a vane pump vacuum). The oily crude product is dissolved in pyridine (20 ml) at 0° C. and tosyl chloride (7.2 g; 48 mmol; 1.2 equiv) is added in small portions. The solution is taken to ambient temperature and stirred overnight. Water (10 ml) is then added and the product is extracted with dichloromethane (3×20 ml), dried over sodium sulphate and concentrated under reduced pressure in order to produce the title compound (7 g; 29 mmol; 72%).

Workup

  1. extractionextracted with dichloromethane (4×20 ml)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated (it
  5. customto be dried under a vane pump vacuum)
  6. dissolutionThe oily crude product is dissolved in pyridine (20 ml) at 0° C.
  7. customis taken to ambient temperature
  8. extractionthe product is extracted with dichloromethane (3×20 ml)
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated under reduced pressure in order

Sources & evidence

ORD record
ord-619000b6c37647479fecf0cd21cb7ad0
Source dataset
uspto-grants-2010_08
Patent number
US07781417B2

Reaction notes

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