4-[(dimethylamino)methyl]benzonitrile → HCID 19993416, compound

HRID 344994Notes

Reaction equation

HRID 344994 reaction equation
[CH:1]1[C:18]2[C:5](=[C:6]([C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[CH2:22][Br:23])[C:7]3[C:16]([CH:17]=2)=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=1)[CH3:29].[PH4+].[AsH4+]>C(#N)C.C(OCC)C>[Br-:23].[C:37]([C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N+:28]([CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([C:6]3[C:7]4[C:16](=[CH:15][C:14]5[C:9]([CH:8]=4)=[CH:10][CH:11]=[CH:12][CH:13]=5)[CH:17]=[C:18]4[C:5]=3[CH:4]=[CH:3][CH:2]=[CH:1]4)[CH:20]=2)([CH3:27])[CH3:29])=[CH:36][CH:35]=1)#[N:38]

Participants

7

Reactant 4

HCID 8263294-[(dimethylamino)methyl]benzonitrileHCID 5460504PhosphoniumHCID 5460506ArsoniumHCID 19993410HCID 19993410, compound

Product 1

HCID 19993416HCID 19993416, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of (B) and N,N-dimethyl-4-cyanobenzylamine in acetonitrile was refluxed for 2 hr. The reaction mixture was then poured into diethyl ether, and the crude product was collected by filtration. The crude product was recrystallized from ethanol. The same reaction can be used to prepare the corresponding phosphonium and arsonium salts.

Workup

  1. temperaturewas refluxed for 2 hr
  2. filtrationthe crude product was collected by filtration
  3. customThe crude product was recrystallized from ethanol
  4. customThe same reaction

Sources & evidence

ORD record
ord-170f77478cd344a1a077d6f87d7c2d30
Source dataset
uspto-grants-1991_10
Patent number
US05055376

Reaction notes

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