Water → HCID 22612128, compound

HRID 843986Notes

Reaction equation

HRID 843986 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.O>CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[O:23][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 79333-ChlorophenolHCID 10796Cesium carbonateHCID 810792-Chloronicotinonitrile

Product 1

HCID 22612128HCID 22612128, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution 2-Chloro-nicotinonitrile (5.0 grams, 36.1 mmole), cesium carbonate (23.5 grams, 72.2 mmole) and 3-chlorophenol (4.65 grams, 36.1 mmole) in dimethylformamide (100 ml) was heated to 80° C. over night. The mixture was cooled and poured into 500 ml water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to a white solid (8.21 g). M.P. 88-90° C.; Anal. calcd. for C12H7N2OCl: C, 62.49; H, 3.06; N, 12.15. Found: C, 62.43; H, 3.00; N, 12.13.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with diethyl ether
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a white solid (8.21 g)

Sources & evidence

ORD record
ord-7698ff81876d47828d2e1fb7efa2ac9a
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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