Acetonitrile → HCID 21273621, compound

HRID 1382853Notes

Reaction equation

HRID 1382853 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:10]1[C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[O:13][CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+].C(#N)C>O.CCOCC>[O:10]1[C:14]2([CH2:19][CH2:18][N:17]([C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[C:4]#[N:5])[CH2:16][CH2:15]2)[O:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 678552-Fluorobenzonitrile

Product 1

HCID 21273621HCID 21273621, compoundYield 391.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 23 g (0.0163 mol) o-fluorobenzonitrile, 70 g (0.4889 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 34 g (0.246 mol) of K2CO3, and 150 ml of acetonitrile is stirred at reflux for three days. The reaction mixture is allowed to cool to ambient temperature, diluted with water and extracted with methylene chloride. The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo to give an oil. Trituration with ether furnishes 15.6 g (39%) of title compound: IR (KBr) 2200, 1590 and 1485 cm-1 ; NMR (CDCl3) δ7.65-6.9 (m, 4H), 4.02 (s, 4H), 3.33 (m, 4H), and 1.94 (m, 4H).

Workup

  1. temperatureat reflux for three days
  2. extractionextracted with methylene chloride
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give an oil

Sources & evidence

ORD record
ord-069bfdeebeb34200b72545d961fcf319
Source dataset
uspto-grants-1989_02
Patent number
US04808612

Reaction notes

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