Propanal → HCID 18331459, compound

HRID 2270551Notes

Reaction equation

HRID 2270551 reaction equation
[CH:1](=O)[CH2:2][CH3:3].C(Cl)(Cl)Cl.BrBr.[C:11]([O:15][C:16]([NH:18][CH2:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]([NH2:29])=[S:28])[CH:23]=[CH:24][CH:25]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(N(CC)CC)C.CC(C)=O.O1CCOCC1>[C:11]([O:15][C:16]([NH:18][CH2:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]2[S:28][C:2]([CH3:3])=[CH:1][N:29]=2)[CH:23]=[CH:24][CH:25]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

8

Reactant 4

HCID 527PropanalHCID 6212ChloroformHCID 24408BromineHCID 18331431HCID 18331431, compound

Product 1

HCID 18331459HCID 18331459, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of propionaldehyde (72 μl), chloroform (1 ml) and 1,4-dioxane (1 ml), bromine (52 μl) was added. The reaction mixture was stirred at room temperature for 30 min and then N-(3-(t-butoxycarbonylaminomethyl)phenyl)thiourea (262 mg), acetone (2 ml) and triethylamine (0.14 ml) were added. The reaction mixture was heated under reflux for 3.5 h and concentrated under reduced pressure. To the resulting residue, water was added and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (eluent, methylene chloride:methanol=99:1) to give 79.2 mg of the titled compound (yield, 27%).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 3.5 h
  4. concentrationconcentrated under reduced pressure
  5. additionTo the resulting residue, water was added
  6. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by basic silica gel column chromatography (eluent, methylene chloride:methanol=99:1)

Sources & evidence

ORD record
ord-b8b15c6d49a1490fa69c0b440d43a0e6
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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