Water → 2-(5-t-Butyloxadiazol-3-yl)-3-chloro-2'-methyl-4'-trifluoromethoxybenzanilide

HRID 478946Notes

Reaction equation

HRID 478946 reaction equation
[C:1]([C:5]1[O:9][NH:8][N:7]([C:10]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](Cl)=[O:13])[CH:6]=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].C(N(CC)CC)C.O>O1CCCC1>[C:1]([C:5]1[O:9][NH:8][N:7]([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:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27755462-Methyl-4-(trifluoromethoxy)anilineHCID 180033352-(5-t-Butyloxadiazol-3-yl)-3-chlorobenzoyl chloride

Product 1

HCID 180033382-(5-t-Butyloxadiazol-3-yl)-3-chloro-2'-methyl-4'-trifluoromethoxybenzanilideYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 Gram of 2-(5-t-butyloxadiazol-3-yl)-3-chlorobenzoyl chloride was dissolved in 30 ml of tetrahydrofuran, and 0.3 g of 2-methyl-4-trifluoromethoxyaniline and 0.2 g of triethylamine were added thereto, the reaction was carried out for 1 hour under stirring. After completion of the reaction, the reaction mixture was poured into water, after extraction of the objective product with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure, the residue thus obtained was purified by a silica gel column chromatography to obtain 0.22 g (yield: 29%) of the objective product.

Workup

  1. customAfter completion of the reaction
  2. extractionafter extraction of the objective product with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue thus obtained
  6. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-46b911b38fe9446d812cefdcf33b7e27
Source dataset
uspto-grants-2003_11
Patent number
US06642379B1

Reaction notes

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