Sodium hydride → 1-[(Methanesulfonyl)amino]nonan-4-yl acetate

HRID 1763692Notes

Reaction equation

HRID 1763692 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].Cl[CH2:9][CH2:10][CH2:11][CH:12]([O:18][C:19](=[O:21])[CH3:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>C1C=CC=CC=1.CN(C)C=O>[C:19]([O:18][CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10][CH2:9][NH:7][S:4]([CH3:3])(=[O:6])=[O:5])(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 131047161-Chloro-4-acetoxynonane

Product 1

HCID 203109551-[(Methanesulfonyl)amino]nonan-4-yl acetate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (2 g., 0.083 mole) is suspended in benzene (60 ml.) and dimethylformamide (120 ml.). Methanesulfonamide (7.6 g., 0.08 mole) is added and the suspension is heated on the steam bath for two hours. After the mixture is cooled in an ice bath, 1-chloro-4-acetoxynonane (18.5 g., 0.084 mole) is added dropwise with stirring over one hour. The suspension is heated on the steam bath for twenty hours and separated between ethyl acetate and water. After being washed with water, the organic layer is dried over anhydrous magnesium sulfate. Evaporation of the ethyl acetate in vacuo and distillation through a short path column gives the title compound, 11.6 g. (52%), b.p. 182°-185° C./0.08 mm. Anal. Calcd. for C12H25NO4S: C, 51.58; H, 9.02; N, 5.01. Found: C, 52.33; H, 8.84; N, 4.91.

Workup

  1. temperaturethe suspension is heated on the steam bath for two hours
  2. temperatureAfter the mixture is cooled in an ice bath
  3. temperatureThe suspension is heated on the steam bath for twenty hours
  4. customseparated between ethyl acetate and water
  5. washAfter being washed with water
  6. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  7. customEvaporation of the ethyl acetate
  8. distillationin vacuo and distillation through a short path column

Sources & evidence

ORD record
ord-403dc03c6f07446581e52f2e5a7078d8
Source dataset
uspto-grants-1978_09
Patent number
US04112236

Reaction notes

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