Potassium Hydroxide → 3-(6-Chloro-pyrazin-2-yloxymethyl)-benzonitrile

HRID 2182140

Reaction equation

HRID 2182140 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15].[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[Cl:8][C:4]1[N:3]=[C:2]([O:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 785042,6-DichloropyrazineHCID 27346773-(Hydroxymethyl)benzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,6-dichloropyrazine (400 mg, 0.671 mmol), 3-hydroxymethyl-benzonitrile (428 mg, 0.805 mmol), KOH (181 mg, 0.805 mmol) and 18-crown-6 (28 mg, 0.027 mmol) in toluene (10 mL) was stirred at reflux for 6 h and concentrated in vacuo. The residue was partitioned between H2O and ethyl acetate. The aqueous phase was separated and extracted with ethyl acetate twice. The combined organic extracts were washed with water and brine, dried and concentrated in vacuo. The crude product I-3f (667.2 mg) was used for next step without further purification.

Workup

  1. temperatureat reflux for 6 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between H2O and ethyl acetate
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate twice
  6. washThe combined organic extracts were washed with water and brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe crude product I-3f (667.2 mg) was used for next step without further purification

Sources & evidence

ORD record
ord-f5b3e762177d4d5186cb22e5bb85b384
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Linked notes

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