Sodium Bicarbonate → 3-(1,3-Oxazol-2-yl)aniline

HRID 1492455Notes

Reaction equation

HRID 1492455 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 12371737HCID 12371737, compound

Product 1

HCID 123717413-(1,3-Oxazol-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a slurry of stannous chloride dihydrate (11.8 g, 0.05 mol in 35 mL of ethyl acetate under argon at room temperature was added 2-(3-nitro-phenyl)1,3-oxazole (1.95 g, 0.01 mol, from part A). After heating at 80° C. for 20 minutes, the mixture was poured onto crushed ice and made basic (pH 8.5) with saturated sodium bicarbonate. After filtering the resulting solution through a pad of celite to remove insolubles, the organic layer was separated, washed with water and brine, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give 1.64 g of an oil that slowly solidified. 13C-NMR (CDCl3) δ162.1,146.8, 138.3, 129.7, 128.2, 117.0, 116.5, 112.5. m/s (m+H)+ @ 161; MW=160.

Workup

  1. additionthe mixture was poured
  2. customonto crushed ice
  3. filtrationAfter filtering the resulting solution through a pad of celite
  4. customto remove insolubles
  5. customthe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d98bbccb3cea4343832a42f5f08a1529
Source dataset
uspto-grants-1994_12
Patent number
US05374643

Reaction notes

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