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Ethanol → (2-Chloro-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamide

HRID 390758
Notes
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Reaction equation

HRID 390758 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:3]=1[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:8]=1.C([O-])(=O)C.[Na+].C(O)C.[N:37]#[C:38]Br>ClCCl.C1(C)C=CC=CC=1.[OH-].[Na+]>[Cl:1][C:2]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][C:3]=1[CH2:4][N:5]([CH2:6][C:7]1[CH:12]=[C:11]([C:13]([F:15])([F:16])[F:14])[CH:10]=[C:9]([C:17]([F:18])([F:19])[F:20])[CH:8]=1)[C:38]#[N:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 86614964N-(2-chloro-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine

Product 1

HCID 86614965(2-Chloro-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamide

Reagents, catalysts & solvents 3

HCID 1140
Toluene
Solvent
HCID 6344DichloromethaneSolvent
HCID 14798Sodium HydroxideSolvent

Procedure

To the mixture of the compound from Step B (10 gm), 5.6 gm of sodium acetate 100 mL of ethanol was added over 15 minutes 15.5 mL of cyanogen bromide 3M in dichloromethane. The reaction mixture was stirred at ambient temperature until reaction completion. When the reaction was judged complete, it was diluted with 200 mL of toluene and 200 mL of sodium hydroxide. The layers were separated and the organic layer dried with magnesium sulfate, filtered and concentrated to an oil.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-fe45b772089d4b03b69c7b0a6a989c85
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383660B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes