Tert-Butylamine → N-[1,1-dimethylethyl]-3-chloro-alpha-hydroxybenzeneacetamide

HRID 1090615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090615
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]([OH:27])[C:24]([OH:26])=O)[CH:20]=[CH:21][CH:22]=1.[CH3:28][C:29]([CH3:32])([NH2:31])[CH3:30].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:28][C:29]([NH:31][C:24](=[O:26])[CH:23]([OH:27])[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=1)([CH3:32])[CH3:30]

Komponenten

6

Edukt 4

HCID 6385Tert-ButylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 859813-Chloromandelic acid

Produkt 1

HCID 19913633N-[1,1-dimethylethyl]-3-chloro-alpha-hydroxybenzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dicyclohexylcarbodiimide (11.0Sg) was added in portions to a cooled, stirred mixture of 3-chloro-α-hydroxybenzeneacetic acid (10g), 1,1-dimethylethanamine (3.92g, 5.63ml) and 1-hydroxybenzotriazole (7.24g) in dry dimethylformamide (100ml). The mixture was stirred at ambient temperature for 20h., filtered and the filtrate evaporated. The residual oil was taken up in ethyl acetate, filtered, and the filtrate washed sequentially with sodium carbonate solution, hydrochloric acid (2N) and water. The organic layer was dried (MgSO4), filtered, and evaporated to an oil which was chromatographed on silica. Elution with chloroform gave N-[1,1-dimethylethyl]-3-chloro-α-hydroxybenzeneacetamide, 1.71g, as an oil which crystallized on standing, m.p. 93-99° C.

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 20h.
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. filtrationfiltered
  5. washthe filtrate washed sequentially with sodium carbonate solution, hydrochloric acid (2N) and water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to an oil which
  9. customwas chromatographed on silica
  10. washElution with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-66928f118db84009b25d33cb29173b2d
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082840

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