Water → HCID 13674816, compound

HRID 1649984Notes

Reaction equation

HRID 1649984 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[Cl:16][CH2:17][CH:18](OS(C)(=O)=O)[CH3:19].O>C1(C)C=CC=CC=1>[Cl:16][CH2:17][CH:18]([N:11]([C:5]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]=1[CH3:3])[S:12]([CH3:15])(=[O:14])=[O:13])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 686475HCID 686475, compoundHCID 13674815HCID 13674815, compound

Product 1

HCID 13674816HCID 13674816, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5.2 g of a 80% mineral oil dispersion of sodium hydride are added in small portions, at room temperature, to a suspension of 31.5 g (0.158 moles) of N-(2,6-dimethylphenyl)-methanesulfonamide in 400 ml of dry toluene. The resulting mixture is heated slowly, within about one hour, to 100° C., and then 27.3 g (0.158 moles) of 1-chloro-2-methanesulfonyloxy-propane are added dropwise to the mixture at the same temperature within 0.5 hours. The reaction mixture is stirred at 100°-110° C. for 12 hours, thereafter it is cooled, placed into an ice bath, and 100 ml of water are introduced dropwise. The aqueous phase is separated, the toluene phase is washed with 100 ml of water, twice with 100 ml of 1 n aqueous sodium hydroxide and finally with 100 ml of water, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The thick, yellow, oily residue, weighing 33.9 g, is distilled under reduced pressure. 26.15 g of 1-chloro-2-[N-(2,6-dimethylphenyl)-methanesulfonamido]-propane are obtained as a slightly opalescent oil; b.p.: 150°-154° C./26.6 Pa.

Workup

  1. temperatureit is cooled
  2. customplaced into an ice bath
  3. customThe aqueous phase is separated
  4. washthe toluene phase is washed with 100 ml of water, twice with 100 ml of 1 n aqueous sodium hydroxide and finally with 100 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-1944fbba2ec247888b28f9e27272c2f2
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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