Sodium Hydroxide → HCID 136360481, compound

HRID 2188540Notes

Reaction equation

HRID 2188540 reaction equation
[OH-].[Na+].[N+:3]([N:6]=[C:7]1[NH:11][CH2:10][CH2:9][N:8]1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([S:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[N:17][CH:18]=1)([O-:5])=[O:4]>O.C(O)C>[N+:3]([N:6]=[C:7]1[NH:11][CH2:10][CH2:9][N:8]1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([S:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[N:17][CH:18]=1)([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 136360482HCID 136360482, compound

Product 1

HCID 136360481HCID 136360481, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.44 g (11 mmol) of sodium hydroxide dissolved in 30 ml water was added to a suspension containing 1.3 g (3.7 mmol) of ethyl 3-[5-(2-nitroiminoimidazolidin-1-ylmethyl)-2-pyridylthio]propionate (4) in 40 ml of ethanol and stirred at room temperature for 1 hour. The ethanol was distilled away under reduced pressure, and 20 ml of water and 30 ml of ether were added to the residues which were then partitioned, and the aqueous layer was adjusted to pH 5 with dilute hydrochloric acid and extracted twice with 70 ml of ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residues were purified by silica gel chromatography (ethyl acetate: methanol=1:1) to give 0.6 g of (5) (yield 50%).

Workup

  1. additionwas added to a suspension
  2. distillationThe ethanol was distilled away under reduced pressure, and 20 ml of water and 30 ml of ether
  3. additionwere added to the residues which
  4. customwere then partitioned
  5. extractionextracted twice with 70 ml of ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residues were purified by silica gel chromatography (ethyl acetate: methanol=1:1)

Sources & evidence

ORD record
ord-33b69a5b0b5b4ac098cb3974f58e4559
Source dataset
uspto-grants-2012_12
Patent number
US08323904B2

Reaction notes

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