Tetrahydrofuran → HCID 61693364, compound

HRID 931154Notes

Reaction equation

HRID 931154 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Cl[CH:8]([CH3:11])[C:9]#[N:10].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>CCOCC>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH:8]([CH3:11])[C:9]#[N:10])[CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 275241H-Pyrazole, 4-chloro-HCID 5192252-Chloropropionitrile

Product 1

HCID 61693364HCID 61693364, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-1H-pyrazole (4.05 g, 39.5 mmol), 2-chloropropanenitrile (3.71 g, 41.5 mmol), cesium carbonate (15.6 g, 44.3 mmol) and anhydrous tetrahydrofuran (20 mL) were added into a sealed tube and the reaction mixture was heated to 100° C. for 2 h. The mixture was diluted with ether (100 mL) and filtered. The solids were rinsed with ether (30 mL×3) and the filtrate was diluted with dichloromethane (10 mL). The solution was concentrated under reduced pressure to afford the title compound as oil (7.15 g). The material was taken to the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 1.90 (d, 3H), 5.21-5.30 (m, 1H), 7.51 (s, 1H), 7.58 (s, 1H); MS (EI+) (M+) 155; GCMS retention time: 1.23 minutes (Method O).

Workup

  1. filtrationfiltered
  2. washThe solids were rinsed with ether (30 mL×3)
  3. additionthe filtrate was diluted with dichloromethane (10 mL)
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-09832a6e1d614717a8e9ce18a41d8bed
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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