Diisopropylethylamine → HCID 68573992, compound

HRID 225496

Reaction equation

HRID 225496 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]([NH2:18])=[NH:17])[CH:2]=[CH2:3].CN(C)[CH:21]=[CH:22][C:23]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=O.C(N(C(C)C)C(C)C)C>C(O)CCC.C(OCC)(=O)C>[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]1[N:18]=[C:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[CH:21][N:17]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178459007HCID 178459007, compound

Product 1

HCID 68573992HCID 68573992, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A stirred mixture of {2-[(2-propenyloxy)-methyl]-5-nitro-phenyl}-guanidine (3.75 g, 15 mmol), 3-(dimethylamino)-1-(3-pyridinyl)-2-propen-1-one (2.60 g, 15 mmol) and ethyl diisopropylamine (2.6 mL, 15 mmol) in 1-butanol (50 mL) is heated at 120° C. for 20 h. The solvent is then evaporated off under reduced pressure to give a residue which is dissolved in ethyl acetate (100 mL). The resulting mixture is filtered (celite), washed with saturated aqueous sodium chloride (50 mL), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate, and recrystallised from ethyl acetate-hexane to give the title compound as a yellow crystalline solid, m.p. 213-2150C.

Workup

  1. customThe solvent is then evaporated off under reduced pressure
  2. customto give a residue which
  3. filtrationThe resulting mixture is filtered (celite)
  4. washwashed with saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customto yield the crude product which
  9. customis purified by column chromatography on silica gel, eluent ethyl acetate
  10. customrecrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-56d4ff03fd554ab5ade9deb49f7d226d
Source dataset
uspto-grants-2009_07
Patent number
US07557105B2

Linked notes

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