Ethanamine, 2,2,2-trifluoro- → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzhydroxamic acid N-(2,2,2-trifluoroethyl)carbamic acid anhydride

HRID 452527Notes

Reaction equation

HRID 452527 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[F:13][C:14]([F:18])([F:17])[CH2:15][NH2:16].[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2([C:43]([F:46])([F:45])[F:44])[O:31][N:30]=[C:29]([C:32]3[CH:41]=[CH:40][C:35]([C:36]([NH:38][OH:39])=[O:37])=[C:34]([CH3:42])[CH:33]=3)[CH2:28]2)[CH:23]=[C:24]([Cl:26])[CH:25]=1>O1CCCC1>[F:13][C:14]([F:18])([F:17])[CH2:15][NH:16][C:1]([O:39][NH:38][C:36](=[O:37])[C:35]1[CH:40]=[CH:41][C:32]([C:29]2[CH2:28][C:27]([C:22]3[CH:23]=[C:24]([Cl:26])[CH:25]=[C:20]([Cl:19])[CH:21]=3)([C:43]([F:44])([F:46])[F:45])[O:31][N:30]=2)=[CH:33][C:34]=1[CH3:42])=[O:2]

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86611483HCID 86611483, compound

Product 1

HCID 866114844-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzhydroxamic acid N-(2,2,2-trifluoroethyl)carbamic acid anhydrideYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a solution of 0.16 g of carbonyl diimidazole in 2 ml of tetrahydrofuran, 0.10 g of 2,2,2-trifluoroethylamine was added, and stirred at room temperature for 1 hour. Then, a solution of 0.10 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzhydroxamic acid in 2 ml of tetrahydrofuran was added in the reaction mixture, and continued to stir at room temperature further for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of water was added in the residue, and extracted with ethyl acetate (10 ml×1). The organic phase was washed with 5 ml of 2N hydrochloric acid aqueous solution, dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. The residue was purified with silica gel thin-layer chromatography (Kanto Chemical Co., Ltd.: PLC plates silica gel 60 F254 20×20 cm layer thickness 2 mm) that was developed with ethyl acetate-hexane (1:1) to obtain 0.12 g of the aimed product as white crystal.

Workup

  1. stirringto stir at room temperature further for 1 hour
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure, 10 ml of water
  4. additionwas added in the residue
  5. extractionextracted with ethyl acetate (10 ml×1)
  6. washThe organic phase was washed with 5 ml of 2N hydrochloric acid aqueous solution
  7. dry with materialdried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
  8. distillationthe solvent was distilled under reduced pressure
  9. customThe residue was purified with silica gel thin-layer chromatography (Kanto Chemical Co., Ltd.: PLC plates silica gel 60 F254 20×20 cm layer thickness 2 mm) that

Sources & evidence

ORD record
ord-5e8d661b4f86403393dedd6f4a3493f5
Source dataset
uspto-grants-2013_07
Patent number
US08492311B2

Reaction notes

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