Ammonia → HCID 13143661, compound

HRID 1979558Notes

Reaction equation

HRID 1979558 reaction equation
N.[Na].[C:3](#[N:5])[CH3:4].[Cl:6][CH2:7][CH:8]1[CH2:12][O:11][C:10]([C:19]2[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=2[C:21](OC)=[O:22])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9]1>CCOCC>[Cl:6][CH2:7][CH:8]1[CH2:12][O:11][C:10]([C:19]2[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=2[C:21](=[O:22])[CH2:4][C:3]#[N:5])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:9]1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 6342AcetonitrileHCID 5360545Sodium2×HCID 13143660HCID 13143660, compound

Product 1

HCID 13143661HCID 13143661, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a stirring solution of 75 ml of liquid ammonia was added a small piece of sodium and a few crystals of ferric nitrate. A total of 1.15 g (0.0502 mol) of sodium was added over a 20 min period, and after 5 mins a solution of 2.9 ml (0.050 mol) of acetonitrile in 10 ml of ether was added dropwise. A solution of 6.6 g (0.0198 mol) of the end product of Example 12 in 40 ml of ether was added dropwise, and after 2 hrs 100 ml of ether was added and the ammonia was allowed to evaporate. About 100 g of ice was added to the reaction, which was then acidified with acetic acid, followed by neutralization with a saturated solution of sodium bicarbonate. The water layer was separated and extracted once more with ether. The combined ether layers were washed with 100 ml of water, dried over sodium sulfate and evaporated. The oil was dissolved in 15 ml of dichloromethane and filtered through 100 g of Florisil. Elution with dichloromethane, and evaporation gave 2-[4-(chloromethyl)-2-phenyl-1,3-dioxolan-2-yl]-β-oxo-benzenepropanenitrile which was used without further purification.

Workup

  1. customto evaporate
  2. additionAbout 100 g of ice was added to the reaction, which
  3. customThe water layer was separated
  4. extractionextracted once more with ether
  5. washThe combined ether layers were washed with 100 ml of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. dissolutionThe oil was dissolved in 15 ml of dichloromethane
  9. filtrationfiltered through 100 g of Florisil
  10. washElution
  11. customwith dichloromethane, and evaporation

Sources & evidence

ORD record
ord-a2731664b4994d20acfb44c0b9d3431b
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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