Diethyl Ether → HCID 12889639, compound

HRID 894321Notes

Reaction equation

HRID 894321 reaction equation
Cl[C:2](=[N:9][OH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:11]([N:15]=[C:16]=[S:17])[CH:12]=[CH:13][CH3:14].C(OCC)C.C(N(CC)CC)C>O1CCCC1>[N:15]([CH2:11][CH2:12][CH:13]1[O:10][N:9]=[C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:14]1)=[C:16]=[S:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 5442912-Butene, 1-isothiocyanato-HCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 12889639HCID 12889639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 23 g. portion of α-chlorobenzaldoxime, prepared as in Example 1 above, was combined with 17 g. of crotylisothiocyanate in 300 ml. of diethyl ether. The solution was cooled to 15° and 40 ml. of triethylamine in 100 ml. of tetrahydrofuran was added dropwise. The mixture was stirred for 24 hours at 15°, and was then filtered. The filtrate was washed with water, and evaporated to dryness. The residue was dissolved in chloroform, and chromatographed over a column (2.5 cm. diameter by 8 meters long) of polystyrene gel beads. The eluate was evaporated to dryness, and the residue was recrystallized from diisopropyl etherhexane. The product was identified as 10 g. of 5-(2-isothiocyanatoethyl)-3-phenyl-2-isoxazoline, m.p. 54°-56°. The microanalytical results were as follows:

Workup

  1. temperatureThe solution was cooled to 15°
  2. filtrationwas then filtered
  3. washThe filtrate was washed with water
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in chloroform
  6. customchromatographed over a column (2.5 cm. diameter by 8 meters long) of polystyrene gel
  7. customThe eluate was evaporated to dryness
  8. customthe residue was recrystallized from diisopropyl etherhexane
  9. customThe microanalytical results

Sources & evidence

ORD record
ord-3c2e34f3a5bb4aeb940a8d8a76b748ca
Source dataset
uspto-grants-1981_08
Patent number
US04283403

Reaction notes

Loading…