Nitromethane → HCID 21055290, compound

HRID 2215258Notes

Reaction equation

HRID 2215258 reaction equation
[CH2:1]([N:8]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:22]([CH3:25])([O-:24])=[O:23]>C(O)C>[CH2:1]([N:8]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[S:9]([CH2:12][CH2:13][CH2:25][N+:22]([O-:24])=[O:23])(=[O:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 69521435HCID 69521435, compound

Product 1

HCID 21055290HCID 21055290, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude ethanesulfonic acid benzyl-(2,2-diethoxy-ethyl)-amide (10 g, 32 mmol) in ethanol (150 ml) under argon was added nitromethane (100 ml) followed by Na-tert-pentoxide (1.8 g, 16 mmol) at rt. After stirring for overnight at ambient temperature, the mixture was concentrated in vacuo, diluted with chloroform (300 ml), washed with cold 1N HCl (200 ml), dried over MgSO4, filtered, and purified on silica gel column (dichloromethane) to give the title compound (5 g, 42% for 2 steps); 1H NMR (CDCl3): 1.25 (t, 6H), 2.55 (m, 2H), 3.20 (m, 2H), 3.55 (m, 2H), 3.75 (m, 21), 4.60 (m, 5H), 7.40 (m, 5H); LCMS: 393 (MH+).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with chloroform (300 ml)
  3. washwashed with cold 1N HCl (200 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. custompurified on silica gel column (dichloromethane)

Sources & evidence

ORD record
ord-ad443d3e6af9494a8acc52d5e4eedab3
Source dataset
uspto-grants-2006_09
Patent number
US07109233B2

Reaction notes

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