Hydrochloric Acid → 3-(6-Chloro-pyrazin-2-yloxymethyl)-benzonitrile

HRID 2182135

Reaction equation

HRID 2182135 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1.[H-].[Na+].Cl>C1COCC1>[Cl:11][C:12]1[N:13]=[C:14]([O:1][CH2:2][C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])[CH:15]=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 27346773-(Hydroxymethyl)benzonitrile

Product 1

HCID 224819733-(6-Chloro-pyrazin-2-yloxymethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxymethyl-benzonitrile (2.0 g, 15.0 mmol) and 2,6-dichloro-pyrazine (2.24 g, 15.0 mmol) in THF (150 mL) was added 60% NaH in mineral oil (0.9 g, 22.5 mmol). After stirring at ambient temperature for 2 h, the reaction mixture was poured into 1N HCl (100 mL) and extracted with Ethyl Acetate (1×250 mL). The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated to dryness. The crude material was chromatographed over Silica Gel (40 g) eluting with hexanes (1000 mL) followed by ethyl acetate (500 mL) to obtain 3.53 g of the desired pure product (I-3a) as a white solid.

Workup

  1. extractionextracted with Ethyl Acetate (1×250 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude material was chromatographed over Silica Gel (40 g)
  7. washeluting with hexanes (1000 mL)
  8. customto obtain 3.53 g of the desired pure product (I-3a) as a white solid

Sources & evidence

ORD record
ord-ecd8b6d06012422eaeba14a71b48fdf5
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Linked notes

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