Triethylamine → HCID 19010448, compound

HRID 1741592Notes

Reaction equation

HRID 1741592 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:7]=[N+:8]([O-])[CH:9]=[CH:10][CH:11]=1.C[Si]([C:20]#[N:21])(C)C.C(N(CC)CC)C>C(#N)C>[C:20]([C:7]1[C:6]([O:5][C:4]2[CH:13]=[CH:14][CH:15]=[C:2]([F:1])[CH:3]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 19010447HCID 19010447, compound

Product 1

HCID 19010448HCID 19010448, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 33.44 g of 3-(3-fluorophenoxy)pyridine N-oxide, 64.6 ml of trimethylsilyl cyanide and 45.9 ml of triethylamine in 180 ml of acetonitrile was refluxed for 4 hours. After the reaction mixture was concentrated, 200 ml of methylene chloride and 100 ml of 2M aqueous potassium carbonate was added to the residue and the mixture was stirred for a few minutes. The organic layer separated was washed with 50 ml of water, dried over anhydrous sodium sulfate, and concentrated. The solid obtained was washed with isopropyl ether to yield 28.30 g of pale brown crystals, which were recrystallized from ethyl acetate to give slightly brown crystals, mp 92°-93° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationAfter the reaction mixture was concentrated
  3. addition200 ml of methylene chloride and 100 ml of 2M aqueous potassium carbonate was added to the residue
  4. customThe organic layer separated
  5. washwas washed with 50 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe solid obtained
  9. washwas washed with isopropyl ether

Sources & evidence

ORD record
ord-9c1aad21690c4276aef1732f1bb6809d
Source dataset
uspto-grants-1994_08
Patent number
US05334594

Reaction notes

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