Dimethylformamide → HCID 10591183, compound

HRID 440882Notes

Reaction equation

HRID 440882 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=3[O:21][CH3:22])[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Cu][C:24]#[N:25].[CH3:26][N:27](C=O)C>>[C:26]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:24]#[N:25])=[CH:16][C:15]=3[O:21][CH3:22])[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1)#[N:27]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10764575HCID 10764575, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 10591183HCID 10591183, compoundYield 40%

Procedure

A suspension of the dibromo compound of Example 13 (8.4 g, 0.02 mole) and copper(I)cyanide (4.45, 0.05 mole) in 40 mL dry DMF is heated at reflux under nitrogen for 30 hr (TLC followed). The excess DMF is distilled under vacuum and the residue triturated with 100 mL water and stirred with 500 mL 10% sodium cyanide (aqueous) for 1 hr, filtered, washed with water and dried. The solid is subjected to soxlet extraction with acetone (24 hr) followed by chromatography over neutral aluminumoxide, elution with ether:CHCl3 (8:2) to chloroform, to yield a white crystalline solid. Recrystallized from CHCl3 :ether (1:4) yielded 2.5 g of a white solid (40%) having a mp 239-240° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 30 hr (TLC followed)
  3. distillationThe excess DMF is distilled under vacuum
  4. customthe residue triturated with 100 mL water
  5. filtrationfiltered
  6. washwashed with water
  7. customdried
  8. extractionextraction with acetone (24 hr)
  9. washfollowed by chromatography over neutral aluminumoxide, elution with ether:CHCl3 (8:2) to chloroform
  10. customto yield a white crystalline solid
  11. customRecrystallized from CHCl3 :ether (1:4)

Sources & evidence

ORD record
ord-d6cd263eb9f845e190869795ed7a71d8
Source dataset
uspto-grants-1996_05
Patent number
US05521189

Reaction notes

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