Triethylamine → 5-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole

HRID 842100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842100
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1.[CH3:19][CH:20]([OH:23])[C:21]#[CH:22].C(N(CC)CC)C>C1(C)C=CC=CC=1.[Cu]I>[Cl:18][C:4]1[CH:3]=[C:2]([C:22]#[C:21][CH:20]([OH:23])[CH3:19])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 46392547-Bromo-5-chloro-2-(2-chlorophenyl)-1,3-benzoxazole

Produkt 1

HCID 46392555-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

15.98 g (46.6 mmol) of 7-bromo-5-chloro-2-(2-chlorophenyl)-benzoxazole and 5 5.48 ml (69.9 mmol) of (±)-3-butyn-2-ol were heated for 6 h at 90-5° C. in 47 ml of toluene with 47 ml of triethylamine, 163.5 mg (233 μmol) of bis-triphenylphosphine-palladium(II)-dichloride and 8.9 mg (46.6 23 μmol) of copper(I) iodide. The reaction was filtered and the solid washed with toluene. The filtrate was evaporated in vacuo to dryness, the residue taken up in 150 ml of dichloromethane, extracted twice with 50 ml of 1 N HCl, dried with sodium sulfate, and filtered through 120 g of silica gel in a column. The title compound (11.11 g) was recovered as an off-white solid. A recrystallized sample from di-isopropyl ether had mp 129-31° C.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. washthe solid washed with toluene
  3. customThe filtrate was evaporated in vacuo to dryness
  4. extractionextracted twice with 50 ml of 1 N HCl
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered through 120 g of silica gel in a column
  7. customThe title compound (11.11 g) was recovered as an off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-67031ac3d51842e2b56c7159d7e2d5c1
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372770B1

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