Triethylamine → HCID 12360579, compound

HRID 1076686Notes

Reaction equation

HRID 1076686 reaction equation
Cl.[C:2](=[N:10][OH:11])(Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.I[C:13]([CH:15]1[CH2:17][CH2:16]1)=[CH2:14].C(N(CC)CC)C>C(O)C>[CH:15]1([C:13]2[O:11][N:10]=[C:2]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:14]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21537891HCID 21537891, compoundHCID 85615038HCID 85615038, compound

Product 1

HCID 12360579HCID 12360579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred mixture containing 1.35 g. of nicotinoyl chloride oxime hydrochloride and 2.6 g. of 1-iodovinylcyclopropane in 50 ml. of ethanol is added dropwise over a 1 hour period, a solution of 4.27 g. of triethylamine in 40 ml. of ethanol. The reaction is stirred for 1 hour and then the solvent is removed under reduced pressure. The residue is dissolved in water and ether and the ether layer is separated. The water layer is extracted twice with ether and then the combined ether layers are dried over sodium sulfate. Filtration and removal of the solvent under reduced pressure gives an orange-yellow solid. This material is recrystallized from isopropyl alcohol to give white crystals, melting point 74°-75°C., nmr spectrum δ6.82 (DMSO-d6, s, 4-isoxazolyl H).

Workup

  1. additionTo a stirred mixture containing 1.35 g
  2. customthe solvent is removed under reduced pressure
  3. dissolutionThe residue is dissolved in water
  4. customether and the ether layer is separated
  5. extractionThe water layer is extracted twice with ether
  6. dry with materialthe combined ether layers are dried over sodium sulfate
  7. filtrationFiltration and removal of the solvent under reduced pressure
  8. customgives an orange-yellow solid
  9. customThis material is recrystallized from isopropyl alcohol
  10. customto give white crystals, melting point 74°-75°C., nmr spectrum δ6.82 (DMSO-d6, s, 4-isoxazolyl H)

Sources & evidence

ORD record
ord-66bfe2541d584678a3974aeeda07d2a4
Source dataset
uspto-grants-1976_05
Patent number
US03957805

Reaction notes

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