Hydrochloric Acid → HCID 15148010, compound

HRID 431431Notes

Reaction equation

HRID 431431 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].C(N(CC)CC)C.Cl>C(Cl)(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][Cl:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 123612-(Chloroethoxy)ethanol

Product 1

HCID 15148010HCID 15148010, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a round bottom flask 9.53 g (50 mmol) of p-Toluenesulfonylchloride were mixed with 7.47 g (60 mmol) 2-(2-Chloroethoxy)ethanol in 50 ml CHCl3. The mixture was stirred and cooled below 5° C. and 10.1 g (100 mmol) triethylamine were added drop-wise at this temperature. After the addition was completed, the mixture was stirred for another 3 h at room temperature. At which point, a mixture of 50 g ice and 20 ml conc. HCl was added carefully and stirred for 30 min. The chloroform phase was separated, washed three times with 30 ml water, dried with Na2SO4 and the solvent removed in vacuo upon which 12.5 g (90%) of a yellowish oil was obtained. The product was used without further purification.

Workup

  1. temperaturecooled below 5° C.
  2. additionAfter the addition
  3. stirringthe mixture was stirred for another 3 h at room temperature
  4. additionwas added carefully
  5. stirringstirred for 30 min
  6. customThe chloroform phase was separated
  7. washwashed three times with 30 ml water
  8. dry with materialdried with Na2SO4
  9. customthe solvent removed in vacuo upon which 12.5 g (90%) of a yellowish oil
  10. customwas obtained
  11. customThe product was used without further purification

Sources & evidence

ORD record
ord-753d0dc6afe2498fac5e8e8679a2d1ff
Source dataset
uspto-grants-2003_12
Patent number
US06660526B2

Reaction notes

Loading…