Methanesulfonyl chloride → 4-(Methanesulfonylamino)benzenebutanol methanesulfonate

HRID 1789450Notes

Reaction equation

HRID 1789450 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:13][S:14]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:14]([CH3:13])(=[O:16])=[O:15])=[CH:7][CH:6]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 150062264-(4-Aminophenyl)butan-1-OL

Product 1

HCID 545258984-(Methanesulfonylamino)benzenebutanol methanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

9.25 g (0.056 mole) 4-aminobenzenebutanol is dissolved in 100 ml pyridine and the solution is cooled to ca. -10° C. 17.33 ml (25.65 g) (0.244 mole) methanesulfonyl chloride is added dropwise with vigorous stirring at a rate such that the methanesulfonyl chloride is added, the reaction mixture is left in the freezer for two days. The reaction mixture is poured onto 300 ml ice water and extracted with 3×200 ml methylene chloride. The combined organic layers are washed with 1 liter cold 5% HCl in 3 portions. The organic layer is dried over sodium sulfate, filtered, and stripped. The residue is crystallized from ethyl acetate/ether to obtain the title compound.

Workup

  1. additionis added
  2. extractionextracted with 3×200 ml methylene chloride
  3. washThe combined organic layers are washed with 1 liter cold 5% HCl in 3 portions
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customThe residue is crystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-e58ccd8a18b34601959a020e8d497689
Source dataset
uspto-grants-1987_08
Patent number
US04689341

Reaction notes

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