Methylamine → 1-(2-isopropyloxazol-4-yl)-N-methylmethanamine

HRID 1736600Notes

Reaction equation

HRID 1736600 reaction equation
[CH3:1][NH2:2].Cl[CH2:4][C:5]1[N:6]=[C:7]([CH:10]([CH3:12])[CH3:11])[O:8][CH:9]=1>O1CCOCC1.O>[CH:10]([C:7]1[O:8][CH:9]=[C:5]([CH2:4][NH:2][CH3:1])[N:6]=1)([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27632914-(Chloromethyl)-2-(propan-2-yl)-1,3-oxazole

Product 1

HCID 108207841-(2-isopropyloxazol-4-yl)-N-methylmethanamineYield 71%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 40% aqueous methylamine (100 mL) was added dropwise a suspension of 4-chloromethyl-2-isopropyloxazole (4.20 g, 0.0263 mol)in p-dioxane/H2O (1:1 (v/v), 20 mL) over a 25 min period. After stirring for 45 min at ambient temperature, the volume was reduced to ca. 50 mL by rotary evaporation in vacuo, and NaCl was added. The aqueous was extracted with CHCl3 (4×100 mL), and the combined extract was dried over Na2SO4 and concentrated in vacuo. The resulting brown liquid was chromatographed on a 200 g SiO2 flash column with 2% iPrNH2 /CH2Cl2 followed by a gradient of iPrNH2 /MeOH/CH2Cl2 (0.5:2:97.5, 0.5:4:95.5). Concentration in vacuo of the product-containing fractions afforded the desired compound as a golden oil (2.89 g, 0.0187 mol, 71%): 1H NMR (CDCl3) δ1.33 (d, J=6.9 Hz, 6H), 2.46 (s, 3H), 2.99-3.14 (m, 1H), 3.64 (s, 2H), 7.42 (s, 1H). Mass spectrum: (M+H)+ =155, (M+NH4)+ =172.

Workup

  1. customthe volume was reduced to ca. 50 mL by rotary evaporation in vacuo, and NaCl
  2. additionwas added
  3. extractionThe aqueous was extracted with CHCl3 (4×100 mL)
  4. extractionthe combined extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting brown liquid was chromatographed on a 200 g SiO2 flash column with 2% iPrNH2 /CH2Cl2
  8. concentrationConcentration in vacuo of the product-containing fractions

Sources & evidence

ORD record
ord-10678fd5072040b3abc43de6c520374f
Source dataset
uspto-grants-1996_07
Patent number
US05541206

Reaction notes

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