4-Chlorophenol → HCID 24777022, compound

HRID 2276828Notes

Reaction equation

HRID 2276828 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)O.[NH2:29][C:30]([NH2:32])=[NH:31]>CN(C)C(=O)C.CN(C)C=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:3]=2[C:4]([NH2:5])=[N:31][C:30]([NH2:32])=[N:29]3)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 746952,6-DifluorobenzonitrileHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 24777022HCID 24777022, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

10.0 g (71.89 mmol) of 2,6-difluorobenzonitrile, 10.17 g (79.08 mmol) of 4-chlorophenol and 19.87 g (143.78 mmol) of potassium carbonate were added into 300 ml of N,N-dimethylformamide, and stirred at 50° C. for 10 h to complete the reaction. The reaction mixture was evaporated to dryness, diluted with 200 ml water and extracted with 400 ml ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and evaporated to dryness. The residue was passed through column chromatography to provide an intermediate. The intermediate and 17.41 g (143.78 mmol) of guanidine carbonate were heated to 140° C. in 300 ml of N,N-dimethylacetamide and reacted for 8 h to complete the reaction. The reaction mixture was evaporated to dryness, diluted with 200 ml of water and extracted with 400 ml of dichloromethane. The organic layer was dried with anhydrous sodium sulfate and evaporated to dryness. The residue was passed through column chromatography to provide 13.7 g of compound Yhhu-0968 with a total yield of 67% in the two steps).

Workup

  1. customthe reaction
  2. customThe reaction mixture was evaporated to dryness
  3. additiondiluted with 200 ml water
  4. extractionextracted with 400 ml ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customto provide an intermediate
  8. customreacted for 8 h
  9. customthe reaction
  10. customThe reaction mixture was evaporated to dryness
  11. additiondiluted with 200 ml of water
  12. extractionextracted with 400 ml of dichloromethane
  13. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  14. customevaporated to dryness

Sources & evidence

ORD record
ord-822874875def476ebf7025c7367ba552
Source dataset
uspto-grants-2015_09
Patent number
US09133138B2

Reaction notes

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