Acetyl chloride → N-[(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamide

HRID 589070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589070
[C:1](Cl)(=[O:3])[CH3:2].[N+:5]([C:8]1[C:13]2[NH:14][C:15]([CH2:24][NH2:25])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][O:17][C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:7])=[O:6]>C(Cl)Cl.C(N(CC)C(C)C)(C)C>[N+:5]([C:8]1[C:13]2[NH:14][C:15]([CH2:24][NH:25][C:1](=[O:3])[CH3:2])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][O:17][C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:7])=[O:6]

Komponenten

5

Edukt 2

HCID 6367Acetyl chlorideHCID 904100791-(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methanamine

Produkt 1

HCID 90409716N-[(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

Acetyl chloride (15 μL, 0.21 mmol) was added to a mixture of 1-(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methanamine (50 mg, 0.2 mmol) in methylene chloride (3 mL), N,N-diisopropylethylamine (60 μL) and was stirred at room temperature for 1 h. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude N-[(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methyl]acetamide (0.040 g. 70%). LCMS calculated for C16H17N4O4 (M+H)+: m/z=329.1. found: 329.0.

Aufarbeitung

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-691234e4504544cd90ba224fc0519b63
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227985B2

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