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Monobenzone → 3-[4-(Benzyloxy)phenoxy]-6-chloro-2-pyrazinecarbonitrile

HRID 392333
Notes
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Reaction equation

HRID 392333 reaction equation
Cl[C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=1.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:2]2[C:3]([C:9]#[N:10])=[N:4][C:5]([Cl:8])=[CH:6][N:7]=2)=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7638MonobenzoneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 226628453,6-Dichloropyrazine-2-carbonitrile

Product 1

HCID 226627883-[4-(Benzyloxy)phenoxy]-6-chloro-2-pyrazinecarbonitrileYield 79.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

In 25 mL of dimethylformamide was dissolved 2.5 g of 3,6-dichloro-2-pyrazinecarbonitrile. After adding 3.2 g of 4-(benzyloxy)phenol and 3.0 g of potassium carbonate, the mixture was stirred at room temperature for one hour. A mixture of 25 ml of ethyl acetate and 100 mL of water was added to the reaction mixture, and the organic layer was separated. The organic layer thus obtained was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Diisopropyl ether was added to the residue, the insoluble matter was filtered off, and the filtrate was concentrated. The residue thus obtained was washed with n-hexane to obtain 3.84 g of 3-[(4-(benzyloxy)phenoxy)]-6-chloro-2-pyrazinecarbonitrile as a light brown-colored solid product.

Workup

  1. additionwas added to the reaction mixture
  2. customthe organic layer was separated
  3. customThe organic layer thus obtained
  4. washwas washed successively with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. additionDiisopropyl ether was added to the residue
  8. filtrationthe insoluble matter was filtered off
  9. concentrationthe filtrate was concentrated
  10. customThe residue thus obtained
  11. washwas washed with n-hexane

Sources & evidence

ORD record
ord-6f1f6e73e2fc4e46b090e0eba055da6d
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800629B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes