Hydrochloric Acid → Ethyl (5-ethoxypyrazin-2-yl)carbamate

HRID 715525Notes

Reaction equation

HRID 715525 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])(C)C)=[N:6][CH:7]=1.Cl.[CH3:17][CH2:18][O:19]C(C)=O>[O-]CC.[Na+]>[CH2:18]([O:19][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][CH2:11][CH3:14])=[N:6][CH:7]=1)[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86717588tert-Butyl (5-chloropyrazin-2-yl)carbamate

Product 1

HCID 86717589Ethyl (5-ethoxypyrazin-2-yl)carbamateYield 42.9%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

The mixed products from 1,1-dimethylethyl (5-chloro-2-pyrazinyl)carbamate were combined and refluxed in 24% sodium ethoxide for 5 days, then cooled to RT, neutralized with HCl, and the product extracted out with DCM. The DCM was washed with saturated NaHCO3, then concentrated to afford a black residue. Addition of EtOAc afforded solids that were filtered off, washed with EtOAc to give ethyl (5-ethoxypyrazin-2-yl)carbamate as a brown solid (3.5 g, 42.9%).

Workup

  1. extractionthe product extracted out with DCM
  2. washThe DCM was washed with saturated NaHCO3
  3. concentrationconcentrated
  4. customto afford a black residue
  5. filtrationwere filtered off
  6. washwashed with EtOAc

Sources & evidence

ORD record
ord-66e5bca0997f495689b182c904655b6b
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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