Water → HCID 131729807, compound

HRID 1511607Notes

Reaction equation

HRID 1511607 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].O>C(Cl)Cl>[CH2:21]([O:20][C:18](=[O:19])[NH:9][CH2:8][CH2:7][C:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 149337782-(5-Methylfuran-2-yl)ethan-1-amine

Product 1

HCID 131729807HCID 131729807, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(5-Methylfuran-2-yl)ethylamine (1.0 g) prepared in the step 2 and 2.2 mL of triethylamine were dissolved in 25 mL of methylene chloride, 0.87 g of ethyl chloroformate was slowly dropped thereinto under cooling with ice and the mixture was stirred at room temperature for 8 hours. To the reaction solution was added 200 mL of water followed by extracting with methylene chloride. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 0.61 g of the objective compound as yellow liquid.

Workup

  1. temperatureunder cooling with ice
  2. extractionby extracting with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-483f720b113b4cdab8146074e2b26de0
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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