Triethylamine → [5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)ethyl ester

HRID 553668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553668
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([OH:46])[CH3:45]>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:41][C:42]1[CH:50]=[CH:49][CH:48]=[CH:47][C:43]=1[CH:44]([O:46][C:22](=[O:31])[NH:19][C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:45]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 260821-(2-Chlorophenyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Produkt 1

HCID 67350786[5-(4-Bromophenyl)-3-methylisoxazol-4-yl]carbamic acid 1-(2-chlorophenyl)ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (5.764 g, 20.4 mmol) in toluene (200 mL) was added triethylamine (3.13 mL, 22.4 mmol) and diphenylphosphoryl azide (4.42 mL, 20.4 mmol), and the mixture was stirred for 5 minutes at room temperature. 2-Chloro-alpha-methylbenzyl alcohol (3.2 g, 22.4 mol) was added, and the reaction was stirred at 80° C. for 2 hours. The mixture was diluted with EtOAc (200 mL) and extracted with EtOAc. The combined organic layers were washed twice with water and once with brine, and the combined aqueous layers were back-extracted with EtOAc. The combined organic layers were concentrated, and the residue was purified by silica gel chromatography to give [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid 1-(2-chloro-phenyl)-ethyl ester.

Aufarbeitung

  1. stirringthe reaction was stirred at 80° C. for 2 hours
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed twice with water and once with brine
  4. extractionthe combined aqueous layers were back-extracted with EtOAc
  5. concentrationThe combined organic layers were concentrated
  6. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8a30ad3199fc413cb3171766bcbadaf6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048902B2

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