Ethanamine, 2,2,2-trifluoro- → 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxy-N-(2,2,2-trifluoroethyl)acetamide

HRID 1022841Notes

Reaction equation

HRID 1022841 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17](/[CH:20]=[N:21]/[O:22][CH2:23][C:24](O)=[O:25])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.CN(C)CCCN=C=NCC.[F:44][C:45]([F:49])([F:48])[CH2:46][NH2:47]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:29])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17](/[CH:20]=[N:21]/[O:22][CH2:23][C:24]([NH:47][CH2:46][C:45]([F:49])([F:48])[F:44])=[O:25])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 467018012-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetic acid2×

Product 1

HCID 467018032-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxy-N-(2,2,2-trifluoroethyl)acetamideYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-meth-(E)-ylideneaminooxy]-acetic acid (i.e. the product of Step 2, 200 mg) in CH2Cl2 (12 mL) was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (130 mg). After 15 min, 2,2,2-trifluoroethyl amine (64 μL, 80 mg) and N,N-4-dimethylaminopyridine (80 mg) was added and the mixture was stirred at room temperature over night. After concentration in vacuum, the residue was purified by flash chromatography on silica gel to obtain the title compound (100 mg, 43%).

Workup

  1. concentrationAfter concentration in vacuum
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4be84f0f5bd1423ebb727f97d31c368f
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

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