Sodium Hydroxide → HCID 131712081, compound

HRID 1413925Notes

Reaction equation

HRID 1413925 reaction equation
[N:1]([CH2:18][CH2:19][OH:20])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:21][S:22](Cl)(=[O:24])=[O:23].[OH-].[Na+]>C(#N)C.O>[N:1]([CH2:18][CH2:19][O:20][S:22]([CH3:21])(=[O:24])=[O:23])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 2199422-(DIOCTYLAMINO)ETHANOL

Product 1

HCID 131712081HCID 131712081, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

In 200 ml of acetonitrile was dissolved 28.5 g (0.1 mol) of (C8H17)2NCH2CH2OH and then 11.5 g (0.1 mol) of methanesulfonyl chloride was added dropwise to the solution with stirring at 10° C. Then, after stirring the mixture for 3 hours at temperatures below 20° C., the reaction mixture was neutralized carefully with a solution of 4 g (0.1 mol) of sodium hydroxide in 40 ml of water. After concentrating the reaction mixture under reduced pressure, the residue was dispersed in 1 liter of water and the product was extracted with 500 ml of ether. The organic layer obtained was dried by anhydrous magnesium sulfate and then ether was distilled away to provide 27.0 g of (C8H17)2NCH2CH2OSO2CH3.

Workup

  1. stirringThen, after stirring the mixture for 3 hours at temperatures below 20° C.
  2. concentrationAfter concentrating the reaction mixture under reduced pressure
  3. additionthe residue was dispersed in 1 liter of water
  4. extractionthe product was extracted with 500 ml of ether
  5. customThe organic layer obtained
  6. dry with materialwas dried by anhydrous magnesium sulfate
  7. distillationether was distilled away

Sources & evidence

ORD record
ord-71d5d09c42f5433fab67006483dee614
Source dataset
uspto-grants-1981_02
Patent number
US04251626

Reaction notes

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