Sodium hydride → HCID 13674813, compound

HRID 1649980Notes

Reaction equation

HRID 1649980 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].CS(O[CH2:21][CH:22]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH3:23])(=O)=O>C1(C)C=CC=CC=1>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[N:11]([CH2:21][CH:22]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH3:23])[S:12]([CH3:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 319059NSC260518HCID 686475HCID 686475, compound

Product 1

HCID 13674813HCID 13674813, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1.0 g of a 80% mineral oil dispersion of sodium hydride is added in small portions, at room temperature, to a mixture of 6.0 g (30 mmoles) of N-(2,6-dimethylphenyl)-methanesulfonamide and 100 ml of dry toluene, and the resulting mixture is heated to 100° C. within 0.5 hours. 7.0 g (30 mmoles) of 1,2-bis(methanesulfonyloxy)-propane are added to the mixture at 100°-105° C. within one hour, and the reaction mixture is stirred at the same temperature for 5 hours. The mixture is cooled, washed thrice with 20 ml of water, twice with 25 ml of 1 n aqueous sodium hydroxide solution and then thrice with 30 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The resulting oily substance, weighing 5.9 g, is triturated with diethyl ether to obtain 4.4 g (44%) of a crude, solid product, m.p.: 70°-80° C. The crude product is recrystallized twice from isopropanol to obtain 1.85 g (18.5%) of 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-2-methanesulfonyloxy-propane, m.p.: 117°-120° C. This compound is identical with the product obtained according to Method (A).

Workup

  1. temperatureThe mixture is cooled
  2. washwashed thrice with 20 ml of water
  3. dry with materialeach, dried over anhydrous magnesium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customis triturated with diethyl ether
  6. customto obtain 4.4 g (44%) of a crude, solid product, m.p.: 70°-80° C
  7. customThe crude product is recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-e1ec0035589e49fdbc8027534358eaf9
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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