1-Butanol → HCID 71223482, compound

HRID 1913528Notes

Reaction equation

HRID 1913528 reaction equation
C[N:2]([CH3:12])[CH:3]=[C:4]([N+:10]#[C-:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].N[CH:14]1[CH:21]2[CH2:22][CH:17]3C[CH:19]([CH2:23][CH:15]1[CH2:16]3)[CH2:20]2.C(O)CCC>O>[CH:19]12[CH2:23][CH:15]3[CH2:14][CH:21]([CH2:22][CH:17]([CH2:16]3)[CH:12]1[N:2]1[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:10]=[CH:11]1)[CH2:20]2

Participants

5

Reactant 3

HCID 2631-ButanolHCID 253322-AminoadamantaneHCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylate

Product 1

HCID 71223482HCID 71223482, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Ethyl 3-(dimethylamino)-2-isocyanoacrylate (0.50 g), 2-aminoadamantane (0.54 g), and n-butanol (2.5 mL) were added and stirred at 150° C. for 13 hours. To the reaction solution, water was added, and organic matter was extracted with ethyl acetate. The organic layer was concentrated and then purified by silica gel column chromatography (eluting solvent: methylene chloride-methylene chloride/methanol=95/5 and ethyl acetate) to obtain the title compound (0.24 g).

Workup

  1. extractionorganic matter was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel column chromatography (eluting solvent: methylene chloride-methylene chloride/methanol=95/5 and ethyl acetate)

Sources & evidence

ORD record
ord-72a352d3e2b14ab1acccdc1c34338d2e
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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