Dichloromethane → HCID 23347209, compound

HRID 1855973Notes

Reaction equation

HRID 1855973 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]#[N:14].[OH-].[Na+].Cl[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22].C(Cl)Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]([CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[C:13]#[N:14]

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 73122-(Diisopropylamino)ethyl chlorideHCID 14798Sodium HydroxideHCID 2343772-(1-bromonaphthalen-2-yl)acetonitrile

Product 1

HCID 23347209HCID 23347209, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

69 Parts of α-(1-bromo-2-naphthyl)acetonitrile is stirred in 150 parts by volume of 50% sodium hydroxide and then 0.7 parts of benzyltriethylammonium chloride is added to the mixture. To this mixture is added slowly a solution of 41.82 parts of 2-chloro-N,N-diisopropylethylamine in 150 parts by volume of methylene chloride and the resulting mixture is stirred at room temperature for about 2 hours. Then, additional quantities of methylene chloride and water are added to the reaction mixture. The organic layer is then separated, dried over anhydrous sodium sulfate and concentrated to give α-(1-bromo-2-naphthyl)-α-[2-(diisopropylamino)ethyl]acetonitrile, as a solid. This compound is represented by the following structural formula ##STR34##

Workup

  1. customThe organic layer is then separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8701bd3674de421b99f7d9784aff6bef
Source dataset
uspto-grants-1980_08
Patent number
US04217306

Reaction notes

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