Triethylamine → HCID 86658796, compound

HRID 2274612Notes

Reaction equation

HRID 2274612 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-7ff4d31b913d43ffa1772c9aa5d43249
Source dataset
uspto-grants-2015_09
Patent number
US09126981B2

Reaction notes

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