Triethylamine → 4-(5-Oxazolyl)-benzamide

HRID 2042014Notes

Reaction equation

HRID 2042014 reaction equation
[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.CC[N:17](CC)CC.ClC(OCC(C)C)=O.[NH4+].[OH-]>C1COCC1>[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:9]([C:10]([NH2:17])=[O:11])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 27764144-(1,3-Oxazol-5-yl)benzoic Acid

Product 1

HCID 219309994-(5-Oxazolyl)-benzamideYield 48.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(5-oxazolyl)benzoic acid (1.0 g, 5.46 mmol) and Et3N (552 mg, 5.46 mmol) in 25 mL of THF was cooled to 0° C. and ClCOOi-Bu (745 mg, 5.46 mmol) was added dropwise. After the addition was over, the reaction mixture was stirred for additional 5 min and then aq NH4OH (0.63 mL of 28% solution, 10.46 mmol) was added. After overnight stirring, the solvent was evaporated, the residue was taken up in water and basified to pH 9. The precipitated solid was filtered, washed with water and dried over P2O5 in a vacuum desiccator to provide 500 mg (48%) of the 4-(5-oxazolyl)-benzamide: 1H NMR (DMSO-d6) δ 8.50 (s, 1H), 8.20-7.80 (m, 5H).

Workup

  1. additionAfter the addition
  2. stirringAfter overnight stirring
  3. customthe solvent was evaporated
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. dry with materialdried over P2O5 in a vacuum desiccator

Sources & evidence

ORD record
ord-1788f13f5c1a4c61b8c21635e1472899
Source dataset
uspto-grants-2013_11
Patent number
US08586576B2

Reaction notes

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