Dicyclohexylcarbodiimide → N-[(2-chlorophenyl)methyl]-N,3-dihydroxy-2,2-dimethylpropanamide

HRID 1995486

Reaktionsgleichung

Reaktionsgleichung von HRID 1995486
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][NH:17][OH:18].C1(N=C=NC2CCCCC2)CCCCC1>C(O)C.C(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][N:17]([OH:18])[C:4](=[O:5])[C:3]([CH3:8])([CH3:7])[CH2:2][OH:1]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 12811040N-(2-ChlorobenZyl)hydroxylamine

Produkt 1

HCID 13192552N-[(2-chlorophenyl)methyl]-N,3-dihydroxy-2,2-dimethylpropanamideAusbeute 7,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of 3.0 grams (0.025 mole) of 3-hydroxy-2,2-dimethylpropionic acid (Example 12, Step A) and 3.9 grams (0.025 mole) of N-(2-chlorophenyl)methyl hydroxylamine (Example 1, Step A-2) in 65 ml of ethanol was added dropwise a solution of 5.2 grams (0.025 mole) of dicyclohexylcarbodiimide in 25 ml of chloroform. Upon completion of addition the reaction mixture was stirred at ambient temperature for 60 hours. The reaction mixture was concentrated under reduced pressure to give a residual solid. The solid was recrystallized from ethanol, then from ethanol-water to give a solid; mp 229°-230°. The filtrates from the recrystallizations were combined and concentrated under high vacuum to give a residual oil. The residual oil was subjected to column chromatography. Elution was accomplished using 4:1--cyclohexane:ethyl acetate. The appropriate fraction was concentrated under reduced pressure to give a solid. The solid was recrystallized from ethyl acetatehexane to give 0.51 gram of N-[(2-chlorophenyl)methyl]-N,3-dihydroxy-2,2-dimethylpropanamide; mp 130°-132°. The solid was recrystallized a second time from ethyl acetate-cyclohexane to raise the mp to 131°-132°.

Aufarbeitung

  1. additionUpon completion of addition the reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a residual solid
  4. customThe solid was recrystallized from ethanol
  5. customfrom ethanol-water to give a solid
  6. customThe filtrates from the recrystallizations
  7. concentrationconcentrated under high vacuum
  8. customto give a residual oil
  9. washElution
  10. concentrationThe appropriate fraction was concentrated under reduced pressure
  11. customto give a solid
  12. customThe solid was recrystallized from ethyl acetatehexane

Quellen und Nachweise

ORD-Eintrag
ord-177dedbb92b04e3b949724f14e5ed9a8
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04405357

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