Ethanol hydrochloride → HCID 70874377, compound

HRID 2172178Notes

Reaction equation

HRID 2172178 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C@@H:12]2[CH2:16][O:15]C(C)(C)[O:13]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C(O)C.Cl>O1CCCC1>[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C@@H:12]([OH:13])[CH2:16][OH:15])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 70874770HCID 70874770, compound

Product 1

HCID 70874377HCID 70874377, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

While stirring a tetrahydrofuran solution (700 ml) of 2-chloro-1-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)ethyl]-4-nitro-1H-imidazole (196.2 g) at room temperature, 1.0 M hydrochloric acid ethanol solution (1,100 ml) was added thereto and stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure, hexane was added to the residue obtained and concentrated under reduced pressure. Thereafter, ethyl acetate was added thereto and concentrated under reduced pressure. Isopropyl ether was added to the resulting solid and stirred for a while. The precipitated crystal was collected by filtration to afford the title compound as a colorless solid (166.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, hexane
  2. additionwas added to the residue
  3. customobtained
  4. concentrationconcentrated under reduced pressure
  5. additionThereafter, ethyl acetate was added
  6. concentrationconcentrated under reduced pressure
  7. additionIsopropyl ether was added to the resulting solid
  8. stirringstirred for a while
  9. filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-1969beb8f62247ad9ef622b5455bcfe2
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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