Hexachloroethane → 3-Chlorocaprolactam

HRID 849147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 849147
C([CH:8]1[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]1=[O:10])(OC(C)(C)C)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.O1CCOCC1>[Cl:26][CH:15]1[CH2:14][CH2:13][CH2:12][NH:11][C:9](=[O:10])[CH2:8]1

Komponenten

6

Edukt 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 86755018Boc-caprolactam

Produkt 1

HCID 193693183-ChlorocaprolactamAusbeute 129,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Example 228 B) To a solution of 1 g (0.0047 mol) of this Boc-caprolactam product of Example 228 A in 10 mL of anhydrous THF at -78° C. was added 0.005 mol of LiHMDS. After stirring for 30 minutes, 1.2 g (0.005 mol) of hexachloroethane in 5 ml of anhydrous THF was added. The mixture was allowed to warm to 0° C. and was quenched with dilute HCl. The mixture was extracted with EtOAc and the organic layer was washed with 5% HCl, dried (MgSO4), filtered and concentrated to afford a yellow oil. The residue oil was dissolved in 40 mL of 1,4-dioxane (satd. with anhydrous HCl), stirred for 40 minutes, concentrated to afford 0.9 g of 3-chlorocaprolactam as an off-white solid.

Aufarbeitung

  1. customwas quenched with dilute HCl
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with 5% HCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a yellow oil
  8. stirringstirred for 40 minutes
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7dc4311919484ce9b2765bd063945009
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06011028

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