Triethylamine → HCID 13674813, compound

HRID 1649979Notes

Reaction equation

HRID 1649979 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[N:14]([CH2:19][CH:20]([OH:22])[CH3:21])[S:15]([CH3:18])(=[O:17])=[O:16].C(N(CC)CC)C>ClCCCl>[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[N:14]([CH2:19][CH:20]([O:22][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:21])[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13674811HCID 13674811, compound

Product 1

HCID 13674813HCID 13674813, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

31.4 ml (46.6 g, 0.4 moles) of methanesulfonyl chloride are added dropwise, within one hour, to a solution of 94.5 g (0.368 moles) of 1-[N-(2,6-dimethylphenyl)-methane-sulfonamido]-2-propanol and 55.3 ml (40.5 g, 0.4 moles) of trietyl amine in 600 ml of 1,2-dichloroethane. During the addition the mixture is cooled with ice to maintain its temperature at 10°-12° C. The mixture is stirred at room temperature for additional 4 hours and then washed thrice with 100 ml of water, each. The dichloroethane solution is dried over anhydrous magnesium sulfate, the solvent is evaporated under reduced pressure, and the thick, oily residue is triturated with 120 ml of isopropanol. The resulting crystals are filtered off, washed with ice-cold isopropanol and dried. 93.2 g (75.8%) of 1-[N-(2,6-dimethylphenyl)-methane-sulfonamido]-2-methanesulfonyloxy-propane are obtained as a white, crystalline substance melting at 111°-114° C.

Workup

  1. additionDuring the addition the mixture
  2. temperatureis cooled with ice
  3. temperatureto maintain its temperature at 10°-12° C
  4. washwashed thrice with 100 ml of water
  5. dry with materialThe dichloroethane solution is dried over anhydrous magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customthe thick, oily residue is triturated with 120 ml of isopropanol
  8. filtrationThe resulting crystals are filtered off
  9. washwashed with ice-cold isopropanol
  10. customdried

Sources & evidence

ORD record
ord-1a946dce64da475890de1dad2d7e5bbe
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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