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

HRID 2075118Notes

Reaction equation

HRID 2075118 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]

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)cyanamideYield 74%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 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. 7.8 gm (74% yield). The product was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) 7.84 (s, 2H), 7.56 (s, 3H), 7.66 (m, 4H), 7.48 (s, 2H), 4.39 (s, 2H), 4.36 (s, 2H)

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-6f676848fbcf4891929ed8b52ab59fc2
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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