Ethylparaben → Ethyl 4-[(3-chloropyrazin-2-yl)oxy]benzoate

HRID 2191912Notes

Reaction equation

HRID 2191912 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:2].[Cl:13][C:14]1[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:13][C:14]1[C:19]([O:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])=[CH:6][CH:7]=2)=[N:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 10796Cesium carbonateHCID 785752,3-Dichloropyrazine

Product 1

HCID 45031059Ethyl 4-[(3-chloropyrazin-2-yl)oxy]benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-hydroxybenzoic acid ethyl ester (55.21 g, 332.3 mmol) and 2,3-dichloropyrazine (49.50 g, 332.3 mmol) in DMSO (300 mL) was added cesium carbonate (129.9 g, 398.7 mmol). The mixture was heated to 70° C. until the starting material was consumed. The mixture was cooled to RT, diluted with water and DCM, the layers were separated and the aqueous layer was extracted with DCM (2×). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was washed with copious amounts of methanol and dried to give ethyl 4-(3-chloropyrazin-2-yloxy)benzoate.

Workup

  1. customwas consumed
  2. temperatureThe mixture was cooled to RT
  3. additiondiluted with water and DCM
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (2×)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe crude material was washed with copious amounts of methanol
  11. customdried

Sources & evidence

ORD record
ord-7b40902fa665497a89168a6a66a610dc
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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