Triethylamine → HCID 86658796, compound

HRID 2361935Notes

Reaction equation

HRID 2361935 reaction equation
[CH2:1]([NH:4][NH2:5])[CH:2]=[CH2:3].C(N(CC)CC)C.Br[C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(Cl)(Cl)Cl.C(OC(=O)C)C>[CH2:1]([N:4]([C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH2:5])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 81921Allylhydrazine

Product 1

HCID 86658796HCID 86658796, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 70%-allylhydrazine (7.73 ml, 75 mmol) and triethylamine (1048 ml, 75 mmol) in chloroform (25 ml) was added ethyl 2-bromo-2-methylpropanoate (9.75 g, 50 mmol) and the mixture was sittred for 1 hr and then refluxed overnight. The reaction mixture was diluted with ethylacetate (150 ml) and washed with water (100 ml) and brine (100 ml). Then the organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The crude residue was subjected to silica gel column chromatography (eluent: chloroform:methanol=95:5) to obtain the title compound (5.0 g, 54%).

Workup

  1. temperaturerefluxed overnight
  2. washwashed with water (100 ml) and brine (100 ml)
  3. dry with materialThen the organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4ddebb5662fc4e55b9618f16349f49f7
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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