Dichloromethane → N-Methoxy-N,2-dimethylbenzo[d]oxazole-5-carboxamide

HRID 627515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627515
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][C:5]=2[N:6]=1.C(Cl)Cl.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:30][NH:31][O:32][CH3:33]>O.[OH-].[Na+]>[CH3:33][O:32][N:31]([CH3:30])[C:11]([C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1)=[O:13]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 232822842-Methyl-1,3-benzoxazole-5-carboxylic acid

Produkt 1

HCID 86716083N-Methoxy-N,2-dimethylbenzo[d]oxazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a flask containing 2-methylbenzo[d]oxazole-5-carboxylic acid (1.00 g, 5.64 mmol) was added DCM (40 mL) to give a suspension. Carbonyldiimidazole (1.01 g, 6.21 mmol) was added and the mixture remained homogeneous and was stirred at room temperature for 17 hours, then N,O-dimethylhydroxylamine hydrochloride (688 mg, 7.06 mmol) was added and the mixture was stirred at room temperature for 18 hours. The contents were diluted with water and 1 N NaOH and extracted with DCM (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (10-40% EtOAc-DCM) gave the title compound as an amber oil.

Aufarbeitung

  1. customto give a suspension
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. extractionextracted with DCM (4×50 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5a16fe30242c426e986dba08004a17fe
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309222B2

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