Cesium carbonate → HCID 67442189, compound

HRID 1799046Notes

Reaction equation

HRID 1799046 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][N:20]=1>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:7][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][N:20]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 742185-Chloro-2-nitroanilineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 67442189HCID 67442189, compoundYield 700.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a well stirred solution of 5-chloro-2-nitroaniline (2.0 g, 11.0 mmol) in dry N,N-dimethylacetamide (DMA; 15 ml), cesium carbonate (Cs2CO3; 757 mg, 2.3 mmol) and 6-chloronicotinonitrile (193 mg, 1.3 mmol) were added and reaction mixture was heated at 130° C. for 3 h. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate (2×100 ml), and the combined organic layers were washed with water (2×50 ml), brine (20 ml), dried (Na2SO4), filtered and concentrated under reduced pressure to yield 2.5 g of the product.

Workup

  1. customreaction mixture
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. washthe combined organic layers were washed with water (2×50 ml), brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40043bbae09948329d5eb6283d99b199
Source dataset
uspto-grants-2013_01
Patent number
US08344010B2

Reaction notes

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