Triethylamine → HCID 14951342, compound

HRID 2211178Notes

Reaction equation

HRID 2211178 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[NH:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([NH:26][NH2:27])=[O:25].C(N(CC)CC)C>O1CCCC1>[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[NH:21][C:22]1[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]1[O:25][C:1](=[O:2])[NH:27][N:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 149513412-[(2,3-Dimethylphenyl)amino]benzoic acid hydrazide

Product 1

HCID 14951342HCID 14951342, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonyldiimidazole (912.3 mg, 5.63 mmoles) is added to a 0° C. solution of 2-[(2,3-dimethylphenyl)amino]benzoic acid hydrazide (1.041 g, 4.08 mmoles) and triethylamine (608 μl, 4.36 mmoles) in 20 ml of tetrahydrofuran. The reaction is stirred at room temperature for one hour. The volatiles are removed in vacuo, and the residue is dissolved in 1:1 ethyl acetate/ether. The organic solution is washed consecutively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant white solid is purified by flash chromatography with 1:1 hexane/ethyl acetate as eluant to give 968.8 mg (85%) of 5-[2-[(2,3-dimethylphenyl)amino]phenyl]-1,3,4-oxadiazol-2(3H)-one, mp 239°-241° C.

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe residue is dissolved in 1:1 ethyl acetate/ether
  3. washThe organic solution is washed consecutively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant white solid is purified by flash chromatography with 1:1 hexane/ethyl acetate as eluant

Sources & evidence

ORD record
ord-8421632470ee47b7a15cca0f6b892584
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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