Methacrylonitrile → HCID 15984010, compound

HRID 505453Notes

Reaction equation

HRID 505453 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[N:16][OH:17])[CH:13]=3)[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][C:19](=[CH2:22])[C:20]#[N:21].Cl[O-].[Na+]>O1CCCC1>[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15]4[CH2:18][C:19]([CH3:22])([C:20]#[N:21])[O:17][N:16]=4)[CH:13]=3)[CH:8]=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 31368MethacrylonitrileHCID 23665760Sodium HypochloriteHCID 136259179HCID 136259179, compound

Product 1

HCID 15984010HCID 15984010, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of compound obtained from step b above (50 mg, 0.218 mmol) and methylacrylonitrile (29.3 mg, 0.436 mmol) was added tetrahydrofuran (5 ml) and stirred the reaction mixture for 10 minutes at room temperature. To the resulting reaction mixture was added sodium hypochlorite (3 ml) with vigorous stirring, which was continued for 15 hours. The solvent was evaporated under reduced pressure and extracted the compound with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to furnish the title compound. The residue thus obtained was purified by column chromatography using ethylacetate in hexane solvent mixture as eluent to furnish the title compound. Yield: 65 mg.

Workup

  1. customTo the resulting reaction mixture
  2. waitwas continued for 15 hours
  3. customThe solvent was evaporated under reduced pressure
  4. extractionextracted the compound with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea215a2ea23e484e860e338a95be58ee
Source dataset
uspto-grants-2010_08
Patent number
US07781460B2

Reaction notes

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