Dimethylamine → HCID 13055164, compound

HRID 1388888Notes

Reaction equation

HRID 1388888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:17][NH:18][CH3:19]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][N:18]([CH3:19])[CH3:17])=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 12834669HCID 12834669, compound

Product 1

HCID 13055164HCID 13055164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The starting material is prepared as follows: 3.8 g of 3-chloro-6-o-tolyl-benzonitrile (described in Example 3) is brominated as described in Example 2, and the residue dissolved in 25 ml of methylene chloride. The solution is added slowly to that of 14 g of liquid dimethylamine in 100 ml of methylene chloride while stirring at 0°. The mixture is stirred at room temperature for 16 hours, evaporated and the residue stirred with diethyl ether and 1 N hydrochloric acid. The aqueous phase is separated, combined with methylene chloride and basified with cold 2 N aqueous sodium hydroxide. The organic layer is separated, dried and evaporated to yield the 3-chloro-6-(o-dimethylaminomethyl-phenyl)-benzonitrile.

Workup

  1. customThe starting material is prepared
  2. stirringThe mixture is stirred at room temperature for 16 hours
  3. customevaporated
  4. stirringthe residue stirred with diethyl ether and 1 N hydrochloric acid
  5. customThe aqueous phase is separated
  6. customThe organic layer is separated
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-1c58959e882242a0b52cd52d2a225543
Source dataset
uspto-grants-1984_02
Patent number
US04434100

Reaction notes

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