Sodium Acetate → HCID 23081124, compound

HRID 856181Notes

Reaction equation

HRID 856181 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[O:10][CH2:11][C:12]2([CH3:15])[CH2:14][O:13]2)=[CH:4][CH:3]=1.[N+]([C:20]1[NH:21][CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[N:24]=1)([O-])=O.C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:16])[O:10][CH2:11][C:12]2([CH3:15])[O:13][C:20]3=[N:24][C:23]([N+:25]([O-:27])=[O:26])=[CH:22][N:21]3[CH2:14]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 23081433HCID 23081433, compoundHCID 178526857HCID 178526857, compound

Product 1

HCID 23081124HCID 23081124, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Methyloxiran-2-ylmethyl 4-chlorophenylcarbamate (1.1 g, 4.4 mmol) and 2,4-dinitro-1H-imidazole (0.35 g, 2.2 mmol) were suspended in ethanol (1 ml), and the resulting mixture was stirred at room temperature for 24 hours. Then, sodium acetate (0.36 g, 4.4 mmol) and ethanol (2 ml) were added to the mixture followed by stirring under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was added water, and the resulting mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was crystallized from methylene chloride-diethyl ether to afford 2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-chlorophenylcarbamate (0.17 g, yield 22%) as a light yellow solid.

Workup

  1. stirringby stirring
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThe residue was added water
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-5dbcf3bbf6ab4f569d8b361614f74d15
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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