Ethyl Acetate → HCID 21812870, compound

HRID 469763Notes

Reaction equation

HRID 469763 reaction equation
[NH2:1]/[C:2](/[C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:3]\[C:4]#[N:5].O.O.O.O.O.O.O.O.O.O.[S-2:20].[Na+].[Na+].C(OCC)(=O)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[NH2:1]/[C:2](/[C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:3]\[C:4](=[S:20])[NH2:5]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 21812866HCID 21812866, compoundHCID 131731131HCID 131731131, compound

Product 1

HCID 21812870HCID 21812870, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

(Z)-3-amino-4,4-dimethyl-pent-2-enenitrile (26 g, 209.35 mmol), sodium sulfide decahydrate (5.71 g, 73.27 mmol) and tetrabutyl ammonium chloride (9.31 g, 33.49 mmol) in benzene and water (215 mL, 2.5:1, v/v) is stirred at 75° C. under hydrogen sulfide gas for three days. 200 mL of ethyl acetate is added and the layers separated. The organic layer is washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound. Yield 23% over three steps. ESI m/z 159=MH+

Workup

  1. customthe layers separated
  2. washThe organic layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3730f2159afd4d9ebc6d4a3b7243e6e7
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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