Methylamine → HCID 10396954, compound

HRID 380537Notes

Reaction equation

HRID 380537 reaction equation
[CH3:1][NH2:2].[C:3]([O:8][CH2:9][CH3:10])(=[O:7])/[CH:4]=[CH:5]/[CH3:6]>>[CH3:1][NH:2][CH:5]([CH3:6])[CH2:4][C:3]([O:8][CH2:9][CH3:10])=[O:7]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 429065Ethyl trans-crotonate

Product 1

HCID 10396954HCID 10396954, compoundYield 72.1%

Procedure

A solution of 479.2 mL (0.958 mole) methylamine (2M in tetrahydrofuran) was added dropwise to 99.44 gm ethyl crotonate with stirring. After stirring 5 days at room temperature the reaction mixture was concentrated under reduced pressure to remove tetrahydrofuran. The residue was distilled to provide 91.25 gm (72%) of the desired product in 2 fractions. MS(FD): m/e=145 (M+); EA: Calculated for: C7H15NO2: Theory: C, 57.90; H, 10.41; N, 9.65. Found: C, 57.61; H, 10.66; N, 9.88.

Workup

  1. stirringAfter stirring 5 days at room temperature the reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customto remove tetrahydrofuran
  4. distillationThe residue was distilled

Sources & evidence

ORD record
ord-beb9e3447cdb4df7bf10c3c9b613198d
Source dataset
uspto-grants-2001_10
Patent number
US06303627B1

Reaction notes

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