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Ethanol → Ethyl 5-chloro-2-(2-trifluoromethylphenyl)pentanimidoate hydrochloride

HRID 546796
Notes
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Reaction equation

HRID 546796 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])[C:6]#[N:7].[CH2:18]([OH:20])[CH3:19].C(Cl)(=O)C>C(OC)(C)(C)C>[ClH:1].[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:15])([F:16])[F:17])[C:6](=[NH:7])[O:20][CH2:18][CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 668395985-Chloro-2-(2-trifluoromethylphenyl)pentanenitrile

Product 1

HCID 46854983Ethyl 5-chloro-2-(2-trifluoromethylphenyl)pentanimidoate hydrochloride

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

5-Chloro-2-(2-trifluoromethylphenyl)pentanenitrile (2.0 g, 7.64 mmol) was dissolved in ethanol (5.36 mL, 91.72 mmol) at room temperature under nitrogen atmosphere. Then, the solution was cooled to 0° C. Acetyl chloride (4.34 mL, 61.14 mmol) was added dropwise to the solution, and the reaction mixture was stirred at room temperature for 67 hours. The reaction mixture was cooled to 10° C. Traces of seed crystal of the title compound which was obtained by the method similar to this step and tert-butylmethylether (hereinafter referred to as “MTBE”) (40 mL) were added to the reaction mixture and the reaction mixture was stirred. The solid was collected by filtration, washed with MTBE to obtain the title compound (2.14 g, 81.6% yield).

Workup

  1. temperatureThe reaction mixture was cooled to 10° C

Sources & evidence

ORD record
ord-6a8f3885b2c44ce894efbc4ec6172ff1
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935815B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes