Nitrogen → 12-(m-Iodophenyl)dodecyl methane sulfonate

HRID 2106984Notes

Reaction equation

HRID 2106984 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:5]=[CH:6][CH:7]=1.N#N.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[S:24]([O-:26])(=[O:20])(=[O:25])[CH3:23].[CH3:23][S:24]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 947NitrogenHCID 31297Methanesulfonyl chlorideHCID 1458416412-m-Iodophenyldodecanol

Product 2

HCID 85257MethanesulfonateHCID 1458416512-(m-Iodophenyl)dodecyl methane sulfonateYield 139.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12-m-Iodophenyldodecanol (5.88 g, 15.17 mmol) was placed into a flame-dried three-neck 100 ml round-bottomed flask equipped with a reflux condenser and charged with N2. Anhydrous pyridine (30 ml) was added. The mixture was cooled to 0° C. before freshly distilled methanesulfonyl chloride (2.0 ml, 25.96 mmol) was added drop-wise. The reaction mixture was allowed to warm to room temperature. After the reaction mixture had been stirred for several hours, it was poured into ice cold H2O and the resulting precipitate was filtered. The solid was dissolved in ether and extracted with H2O, 1N HCl, and H2O. The ether layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was recyrstallized with a hexanes and ethyl acetate mixture to yield the pure mesylate, compound 9, 12-(m-iodophenyl)dodecyl methane sulfonate (4.95 g, 70.7%).

Workup

  1. customequipped with a reflux condenser
  2. additionwas added drop-wise
  3. additionit was poured into ice cold H2O
  4. filtrationthe resulting precipitate was filtered
  5. dissolutionThe solid was dissolved in ether
  6. extractionextracted with H2O, 1N HCl, and H2O
  7. dry with materialThe ether layer was dried (MgSO4)
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e251e5673e7e4e7db97c1a1c3267aad0
Source dataset
uspto-grants-1990_06
Patent number
US04933157

Reaction notes

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