Dimethylformamide → HCID 21195130, compound

HRID 1067885Notes

Reaction equation

HRID 1067885 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[CH3:32][N:33](C)C=O>O>[C:32]([C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1)#[N:33]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium Cyanide2×HCID 21195147HCID 21195147, compound

Product 1

HCID 21195130HCID 21195130, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
160 °C

Procedure

A mixture of 6-bromo-4′-(4-nitrophenyl)-2,2′:6′,2″-terpyridine (5.63 g), cuprous cyanide (4.66 g), sodium cyanide (2.55 g), and dimethylformamide (35 ml) was heated under argon with stirring to 160° C. for 4.5 hours, cooled to room temperature, and treated with 175 of water. After 15 min, the resulting slurry was filtered, the dark brown paste so obtained was placed in water (85 ml) containing sodium cyanide (3.2 g), and the reaction mixture was stirred for 15 minutes. The solid product was isolated by filtration, washed with water and dried under vacuum. Yield: 4.38 g.

Workup

  1. temperaturewas heated under argon
  2. temperaturecooled to room temperature
  3. waitAfter 15 min
  4. filtrationthe resulting slurry was filtered
  5. customthe dark brown paste so obtained
  6. stirringthe reaction mixture was stirred for 15 minutes
  7. customThe solid product was isolated by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-cdd63ec1700d4036820ac992519943fc
Source dataset
uspto-grants-2001_06
Patent number
US06248870B1

Reaction notes

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