Sodium Bicarbonate → HCID 14479958, compound

HRID 1761669Notes

Reaction equation

HRID 1761669 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 magenesium 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 magenesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-de9ec726bfbe49c99215567f4f7037be
Source dataset
uspto-grants-1989_05
Patent number
US04826990

Reaction notes

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