Dichloromethane → HCID 178470155, compound

HRID 1699726Notes

Reaction equation

HRID 1699726 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:6][C:7]2[C:12]([N:13]=1)=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[C:9](F)[CH:8]=2)[CH3:2].Cl.[OH:24][CH2:25][C:26]1[N:27]=[CH:28][NH:29][CH:30]=1.C(N(CC)CC)C.C(Cl)Cl>C(#N)C>[CH2:1]([O:3][C:4]1[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:6][C:7]2[C:12]([N:13]=1)=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[C:9]([C:28]1[NH:29][CH:30]=[C:26]([CH2:25][OH:24])[N:27]=1)[CH:8]=2)[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 18008883HCID 18008883, compoundHCID 178418488HCID 178418488, compound

Product 1

HCID 178470155HCID 178470155, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-ethoxy-7-fluoro-6-nitroquinoxaline-2-carboxylate (6.90 g, 22.3 mmol) in acetonitrile (70 ml) were added dropwise 4-(hydroxymethyl)imidazole hydrochloride (15.1 g, 112 mmol) and successively triethylamine (23.4 ml, 168 mmol) under shading, and the mixture was refluxed for 16 hours. After cooling, methylene chloride was added to the reaction mixture, which was washed with water. The aqueous layer was extracted with methylene chloride, which was combined with foregoing organic layer. After dried over anhydrous sodium sulfate, solvent was distilled off. The residue obtained was purified by means of silica gel column chromatography [ethyl acetate] to obtain 3.69 g of the the title compound as brown power. Yield 43%. Moreover, 2.15 g of ethyl 3-ethoxy-7-fluoro-6-nitroquinoxaline-2-carboxylate were recovered. Yield 31%.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureAfter cooling
  3. washwas washed with water
  4. extractionThe aqueous layer was extracted with methylene chloride, which
  5. dry with materialAfter dried over anhydrous sodium sulfate, solvent
  6. distillationwas distilled off
  7. customThe residue obtained
  8. customwas purified by means of silica gel column chromatography [ethyl acetate]

Sources & evidence

ORD record
ord-50e7b6d85f964696b61d773aa3269899
Source dataset
uspto-grants-2002_02
Patent number
US06348461B1

Reaction notes

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