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N-(1-hydroxy-2,2,2-trichloroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide → N-(2,2-dichlorovinyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250498
Notes
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Reaction equation

HRID 1250498 reaction equation
O[CH:2]([NH:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:11]=1)=[O:9])[C:3](Cl)([Cl:5])[Cl:4]>C(O)(=O)C.C(OCC)(=O)C.O.[Zn]>[Cl:5][C:3]([Cl:4])=[CH:2][NH:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:28])[F:27])[CH:20]=2)[N:11]=1)=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 18326203N-(1-hydroxy-2,2,2-trichloroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Product 1

HCID 18326227N-(2,2-dichlorovinyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 22728543
Water ethylacetate
Solvent

Conditions

Temperature
50 °C

Procedure

1.0 g (0.0022 mol) of N-(1-hydroxy-2,2,2-trichloroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide was dissolved in about 10 ml of acetic acid. The obtained solution was mixed with 0.29 g (0.0022×2.0 mol) of zinc dust and stirred at about 50° C. for about 5 hours. The reaction solution was distributed in ethyl acetate-water and washed with saturated sodium bicarbonate water and saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. washwashed with saturated sodium bicarbonate water and saturated brine
  2. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-68fb9a2aeeb14befa1536fac4a6208b6
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06339045B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes