Tetrahydrofuran → HCID 69223315, compound

HRID 272628Notes

Reaction equation

HRID 272628 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[NH2:10][C:11]1[O:12][CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]=1[C:16]#[N:17].C(N([CH2:29][CH3:30])CC)C.C1C[O:34]CC1>O>[C:16]([C:15]1[C:14]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:13][O:12][C:11]=1[NH:10][C:7](=[O:8])[CH2:3][C:4]([O:5][CH2:29][CH3:30])=[O:34])#[N:17]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 109209242-Ethylpropanedioyl dichlorideHCID 117898882-amino-4-phenyl-3-furonitrile

Product 1

HCID 69223315HCID 69223315, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl malonyl chloride (3.8 ml, 29.89 mmol) was added dropwise to a solution of 2-amino-4-phenyl-3-furonitrile (5 g, 27.17 mmol) and triethylamine (4.2 ml, 29.89 mmol) in THF (30 ml) maintaining temperature below 5° C. under nitrogen. This was allowed to warm up to room temperature and stirred for 2 hr. The reaction mixture was diluted with water and extracted with DCM. The organic layers were combined and washed with brine and dried over MgSO4. The solution was filtered and solvent removed under reduced pressure. The residue was purified by column chromatography using DCM isolating an orange oil (3.7 g, 46%).

Workup

  1. temperaturemaintaining temperature below 5° C. under nitrogen
  2. extractionextracted with DCM
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. customsolvent removed under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2a78a7a1a94b422d80cadb0eb5bf16c0
Source dataset
uspto-grants-2008_11
Patent number
US07456187B2

Reaction notes

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