Sodium Bicarbonate → HCID 14479958, compound

HRID 2165917Notes

Reaction equation

HRID 2165917 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH3:25])=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=3)[N:13]=2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]([CH3:25])=[C:12]([CH2:14][O:15][C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)[N:13]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 14479956HCID 14479956, compound

Product 1

HCID 14479958HCID 14479958, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.0 g (0.18 mol) of 2-(4-methoxyphenyl)-5-methyl-4-[(3-nitrophenoxy)methyl]oxazole and 20.0 g (0.09 mol) of stannous chloride dihydrate in 150 ml of ethanol is heated to 70° C. for 20 hours. The solution is allowed to cool to room temperature and poured into 2 L of ice water. The mixture is made alkaline by the addition of solid sodium bicarbonate and extracted twice with 500 ml of ethyl acetate. The combined ethyl acetate solution is washed with 500 ml of brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue. Recrystallization from ether/hexane gives 3.8 g (69%) of crystals, m.p. 132°-134° C. The product is used without further purification in subsequent reactions.

Workup

  1. extractionextracted twice with 500 ml of ethyl acetate
  2. washThe combined ethyl acetate solution is washed with 500 ml of brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-8889ff582c33492a87a02514b10a3d72
Source dataset
uspto-grants-1990_07
Patent number
US04942236

Reaction notes

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