Sodium Iodide → HCID 23361961, compound

HRID 1082090Notes

Reaction equation

HRID 1082090 reaction equation
[CH2:1]([N:8]1[CH2:14][N:13]2[C:15]3[C:20]([C:21]4=[C:22](Br)[C:23](Br)=[C:24]5[C:25]6[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=6[N:10]([C:11]5=[C:12]24)[CH2:9]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].[C:35]([Cu])#[N:36].[CH3:38][N:39](C)C(=O)C>ClCCl.O.[NH4+].[OH-]>[CH2:1]([N:8]1[CH2:14][N:13]2[C:15]3[C:20]([C:21]4=[C:22]([C:35]#[N:36])[C:23]([C:38]#[N:39])=[C:24]5[C:25]6[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=6[N:10]([C:11]5=[C:12]24)[CH2:9]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 31374DimethylacetamideHCID 23361965HCID 23361965, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 23361961HCID 23361961, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
190 °C

Procedure

In a 25 mL round bottomed flask, equipped with a reflux condenser, was placed 0.21 g of the compound of Example 5, 105 mg of sodium iodide, 349 mg of CuCN and 10 mL of N,N-dimethyl acetamide. The mixture was heated at 190° C. for 4 hours, cooled to room temperature and diluted with 100 mL dichloromethane, 100 mL water and 12 mL concentrated NH4OH. After stirring rapidly for 15 minutes, the mixture was filtered and the liquid portion was transferred to a separatory funnel. The dichloromethane layer was removed, washed with brine and added over K2CO3. After filtration and evaporation of volatile solvents, the remaining liquid portion was treated with 8 mL of hexane and the resulting precipitate was collected by suction filtration to give 0.11 g of the title compound.

Workup

  1. customIn a 25 mL round bottomed flask, equipped with a reflux condenser
  2. temperaturecooled to room temperature
  3. filtrationthe mixture was filtered
  4. customthe liquid portion was transferred to a separatory funnel
  5. customThe dichloromethane layer was removed
  6. washwashed with brine
  7. additionadded over K2CO3
  8. filtrationAfter filtration and evaporation of volatile solvents
  9. additionthe remaining liquid portion was treated with 8 mL of hexane
  10. filtrationthe resulting precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-104a66f9cf114a98a820720db01bbeb3
Source dataset
uspto-grants-1996_12
Patent number
US05589472

Reaction notes

Loading…