Diethyl Pyrocarbonate → 2-(2-t-Butyloxazol-4-yl)-3-chloro-2'-methyl-4'-trifluoromethoxybenzanilide

HRID 478945

Reaction equation

HRID 478945 reaction equation
[C:1]([C:5]1[O:6][CH:7]=[C:8]([C:10]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1[CH:27]=[C:26]([O:28][C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:24][C:22]=1[NH2:23].CCOC(OC(OCC)=O)=O.C(N(CC)CC)C>O1CCCC1.O>[C:1]([C:5]1[O:6][CH:7]=[C:8]([C:10]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH:23][C:22]2[CH:24]=[CH:25][C:26]([O:28][C:29]([F:30])([F:31])[F:32])=[CH:27][C:21]=2[CH3:20])=[O:14])[N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 27755462-Methyl-4-(trifluoromethoxy)anilineHCID 180033372-(2-t-Butyloxazol-4-yl)-3-chlorobenzoic acid

Product 1

HCID 180033412-(2-t-Butyloxazol-4-yl)-3-chloro-2'-methyl-4'-trifluoromethoxybenzanilideYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.4 Gram of 2-(2-t-butyloxazol-4-yl)-3-chlorobenzoic acid was dissolved in 30 ml of tetrahydrofuran, then 0.3 g of 2-methyl-4-trifluoromethoxyaniline, 0.4 g of DEPC and 0.3 g of triethylamine were added thereto, the resulting mixture was heated under reflux for 3 hours with stirring. After completion of the reaction, the reaction mixture was poured into water, and the objective product was extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, the residue obtained by removal of the solvent by distillation under reduced pressure was purified by the silica gel column chromatography to obtain 0.18 g (yield: 28%) of the objective product.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. extractionthe objective product was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customthe residue obtained by removal of the solvent by distillation under reduced pressure
  7. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-3fa1fdeb772e404ba7e0ae4d9264b74c
Source dataset
uspto-grants-2003_11
Patent number
US06642379B1

Linked notes

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