Benzoyl Peroxide → NCS Chloride

HRID 77495

Reaction equation

HRID 77495 reaction equation
FC1C=CC=C(C)N=1.[CH2:9]1[C:14](=[O:15])[N:13]([Cl:16])[C:11](=[O:12])[CH2:10]1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[CH2:9]1[C:14](=[O:15])[N:13]([Cl:16])[C:11](=[O:12])[CH2:10]1.[Cl-:16]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 960902-Fluoro-6-methylpyridine

Product 1

HCID 86612418NCS Chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Fluoro-6-methylpyridine (1.11 g, 10 mmol), NCS (2.0 g, 15 mmol), and catalytic benzoyl peroxide were dissolved in benzene and heated to reflux overnight. The reaction was concentrated and diluted with water and EtOAc. The organic layer was washed with saturated aq. NaHCO3, dried, filtered, and concentrated. The residue was purified on silica gel to give the desired product.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction was concentrated
  4. additiondiluted with water and EtOAc
  5. washThe organic layer was washed with saturated aq. NaHCO3
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-76c2d06d270544abb8267483dadb4bcd
Source dataset
uspto-grants-2014_09
Patent number
US08841295B2

Linked notes

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