Ethanol → HCID 20496214, compound

HRID 848216Notes

Reaction equation

HRID 848216 reaction equation
[Br:1][C:2]1[N:12]=[CH:11][C:10]([C:13](Br)(Br)Br)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][CH2:18][OH:19].[OH2:20]>[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][C:10]([C:13]([O:19][CH2:18][CH3:17])=[O:20])=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 12919744HCID 12919744, compound

Product 1

HCID 20496214HCID 20496214, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

A mixture of 7 (2.3 g, 0.005 mol), AgNO3 (2.5 g, 0.015 mol) and EtOH (25 mL) was heated on a steam bath. After 1 hour, H2O (25 mL) was added and the yellow solid filtered off. The solution was concentrated to dryness and the residue treated with H2O and extracted with CHCl3 (3X). The CHCl3 layers were washed with NaHSO3 solution, dried, filtered and concentrated to dryness to yield 0.8 g (78%) of 8; 1H NMR (CDCl3) 1.4δ(6H, t, J=7), 4.45 (4H, q, J=7), 8.6 (1H, d, J=3) and 9.0 (1H, d, J=3).

Workup

  1. temperaturewas heated on a steam bath
  2. filtrationthe yellow solid filtered off
  3. concentrationThe solution was concentrated to dryness
  4. additionthe residue treated with H2O
  5. extractionextracted with CHCl3 (3X)
  6. washThe CHCl3 layers were washed with NaHSO3 solution
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-20e8831ee7a24370b1cd754eee4727a4
Source dataset
uspto-grants-1981_10
Patent number
US04294969

Reaction notes

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