Ammonia → 3-(2-Amino-2-cyano-1-propoxy)-4-(2,4-dichlorophenoxy)-benzonitrile

HRID 646196Notes

Reaction equation

HRID 646196 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[O:13][CH2:14][C:15](=O)[CH3:16].[C-:23]#[N:24].[Na+].[NH3:26]>C(O)C>[NH2:26][C:15]([C:23]#[N:24])([CH3:16])[CH2:14][O:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=1[Cl:1])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 686147654-(2,4-Dichlorophenoxy)-3-(2-oxopropoxy)-benzonitrile

Product 1

HCID 686162113-(2-Amino-2-cyano-1-propoxy)-4-(2,4-dichlorophenoxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.2 g of 4-(2,4-dichlorophenoxy)-3-(2-oxopropoxy)-benzonitrile and 4.4 g of sodium cyanide are suspended in 300 ml of a 2M solution of ammonia in ethanol and stirred overnight at room temperature, then filtered and concentrated under vacuum. The residue is dissolved in ethylacetate and washed with water and brine. The organic phase is dried over magnesium sulfate and evaporated under vacuum and the residue recrystallized from ether to yield 3-(2-amino-2-cyano-1-propoxy)-4-(2,4-dichlorophenoxy)-benzonitrile.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue is dissolved in ethylacetate
  4. washwashed with water and brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated under vacuum
  7. customthe residue recrystallized from ether

Sources & evidence

ORD record
ord-a8829c68a86e42ae8a9c1a14f75627d6
Source dataset
uspto-grants-2010_04
Patent number
US07705047B2

Reaction notes

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