Sodium hydride → HCID 53835403, compound

HRID 1763698Notes

Reaction equation

HRID 1763698 reaction equation
[H-].[Na+].[C:3]([O:6][CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:8][CH2:9][CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])(=[O:5])[CH3:4].Br[CH2:22][C:23]1[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=1)[CH:26]=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1C=CC=CC=1.CN(C)C=O>[C:3]([O:6][CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:8][CH2:9][CH2:10][N:11]([CH2:22][C:23]1[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=1)[CH:26]=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[S:12]([CH3:15])(=[O:13])=[O:14])(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 203109551-[(Methanesulfonyl)amino]nonan-4-yl acetateHCID 54157077HCID 54157077, compound

Product 1

HCID 53835403HCID 53835403, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.59 g., 0.025 mole) is suspended in benzene (20 ml.) and dimethylformamide (35 ml.). N-(4-acetoxynonyl)methanesulfonamide [Example 1, Step B] (6.1 g., 0.022 mole) is added and stirred 1 hour at room temperature. Ethyl m-bromomethylcinnamate (6.68 g., 0.025 mole) is added dropwise with stirring over 1 hour. The suspension is stirred at room temperature for 20 hours and then separated between ethyl acetate and water. After being washed with water, the organic layer is dried over anhydrous magnesium sulfate. Removal of the ethyl acetate by evaporation in vacuo gives an oil which, after chromatograpy on silica gel, gives ethyl m-[N-(4-acetoxynonyl)-methanesulfonamidomethyl]cinnamate, 4.1 g. (40% yield). Anal. Calcd. for C24H37NO6S: C, 61.64; H, 7.98; N, 3.00 Found: C, 61.36; H, 8.40; N, 3.07

Workup

  1. stirringwith stirring over 1 hour
  2. stirringThe suspension is stirred at room temperature for 20 hours
  3. customseparated between ethyl acetate and water
  4. washAfter being washed with water
  5. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  6. customRemoval of the ethyl acetate
  7. customby evaporation in vacuo
  8. customgives an oil which

Sources & evidence

ORD record
ord-971829c7d8804095a75938fff3215bc8
Source dataset
uspto-grants-1978_09
Patent number
US04112236

Reaction notes

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