Sodium Bicarbonate → HCID 14479959, compound

HRID 1761670Notes

Reaction equation

HRID 1761670 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 14479957HCID 14479957, compound

Product 1

HCID 14479959HCID 14479959, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20.0 g (0.065 mol) of 5-methyl-4-[(3-nitrophenoxy)methyl]-2-phenyloxazole and 73.0 g (0.325 mol) of stannous chloride dihydrate in 600 ml of ethanol is heated to 70° C. for 3 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 concentrated in vacuo to obtain crystals. Recrystallization from acetone gives 8.5 g (47%) of crystals, m.p. 89°-90° C., MS (CI) 281 (M+H). The product is used without further purification in subsequent reactions.

Workup

  1. extractionextracted twice with 500 ml of ethyl acetate
  2. concentrationThe combined ethyl acetate solution is concentrated in vacuo
  3. customto obtain crystals
  4. customRecrystallization from acetone

Sources & evidence

ORD record
ord-27efbbd4944240f7a82ad969e11c669f
Source dataset
uspto-grants-1989_05
Patent number
US04826990

Reaction notes

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