Hydrochloric Acid → HCID 178510451, compound

HRID 1631315Notes

Reaction equation

HRID 1631315 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].C([O-])([O-])=O.[Cs+].[Cs+].C([O:17][CH:18]=[CH:19][C:20](OCC)=O)C.Cl>CN(C=O)C.O>[OH:17][C:18]1[CH:19]=[CH:20][N:6]2[N:5]=[CH:4][C:3]([C:7]#[N:8])=[C:2]2[N:1]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 855155-Amino-4-cyanopyrazoleHCID 221780Ethyl 3-ethoxy-2-propenoate

Product 1

HCID 178510451HCID 178510451, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (2.70 g, 25.0 mmol) and Cs2CO3 (16.3 g, 50.0 mmol) in dry DMF (70 mL) was added ethyl 3-ethoxyacrylate (5.41 g, 37.5 mmol) and the mixture was heated at 100° C. for 4 hours. The mixture was cooled to ambient temperature and the resultant slurry was poured into deionized H2O (150 mL). The resulting aqueous solution was cooled on an ice bath and concentrated HCl was added slowly with mixing to pH=3.5. The resulting precipitate was collected, washed with H2O followed by Et2O. The solid was dried in vacuum to afford the product as a light beige powder (3.87 g, 97%). MS (apci) m/z=159.0 (M−1).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperatureThe resulting aqueous solution was cooled on an ice bath
  3. additionwith mixing to pH=3.5
  4. customThe resulting precipitate was collected
  5. washwashed with H2O
  6. customThe solid was dried in vacuum

Sources & evidence

ORD record
ord-3b54698aa7f04c2089c0c50d49ce3587
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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