Ethanol → HCID 20496214, compound

HRID 1074613Notes

Reaction equation

HRID 1074613 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 (3×). 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) 1.4 δ (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 (3×)
  6. washThe CHCl3 layers were washed with NaHSO3 solution
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d6b99f3b272e49f4ab612bf53b2b08ff
Source dataset
uspto-grants-1983_07
Patent number
US04393212

Reaction notes

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