4-Toluenesulfonyl chloride → 2-(2-(2-Azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 531419Notes

Reaction equation

HRID 531419 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12])=[N+:2]=[N-:3].C(N(CC)CC)C.[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:27][C:26]1[CH:28]=[CH:29][C:23]([S:20]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 110084382-(2-(2-Azidoethoxy)ethoxy)ethanol

Product 1

HCID 577736862-(2-(2-Azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonateYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution in which the 2-(2-(2-azidoethoxy)ethoxy)ethanol (3.05 g, 17.40 mmol) compound of Chemical Formula 8 was dissolved in methylene chloride (15 mL), 4-dimethylaminopyridine (DMAP) (212.6 mg, 1.74 mmol), triethylamine (TEA) (7.28 mL, 52.20 mmol) and tosyl chloride (3.98 g, 20.88 mmol) were added consecutively at room temperature. The post-reaction mixture obtained after stirring the reaction mixture for 12 hours at room temperature was partitioned to distilled water (40 mL) and ethyl acetate (120 mL). The organic layer was separated, washed with saturated salted water (15 mL), dried with anhydrous sodium sulfate, and vacuum distilled to give 2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (5.15 g, 90%). 1H NMR (500 MHz, CDCl3) δ 7.79 (d, 2H, J=8.2 Hz), 7.33 (d, 2H, J=8.2 Hz), 4.15 (t, 2H, J=5.0 Hz), 3.69 (t, 2H, J=5.0 Hz), 3.63 (t, 2H, J=5.5 Hz), 3.59 (s, 4H), 3.36 (t, 2H, J=5.0 Hz), 2.44 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 144.9, 133.0, 129.9 (2), 128.0 (2), 70.8, 70.7, 70.1, 69.3, 68.8, 50.7, 21.7.

Workup

  1. customThe post-reaction mixture obtained
  2. customwas partitioned
  3. distillationto distilled water (40 mL) and ethyl acetate (120 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated salted water (15 mL)
  6. dry with materialdried with anhydrous sodium sulfate, and vacuum
  7. distillationdistilled

Sources & evidence

ORD record
ord-c211b1847f8e42ed9f8692da1c32a171
Source dataset
uspto-grants-2016_05
Patent number
US09354234B2

Reaction notes

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