Methanesulfonyl chloride → N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide

HRID 2044099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2044099
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17]>N1C=CC=CC=1>[N:18]1([C:16]([C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=2[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[O:17])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 60181686(2-Amino-4-nitrophenyl)(morpholin-4-yl)methanone

Produkt 1

HCID 66833433N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamideAusbeute 14,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (0.179 mL, 2.302 mmol) was added to a solution of (2-amino-4-nitrophenyl)(morpholino)methanone (0.5783 g, 2.302 mmol) in pyridine (3 mL) at 0° C. After 30 min at 0° C., the pyridine solvent was evaporated under reduced pressure. The resulting brown oil was triturated with hot CH2Cl2 and filtered. The filtrate was concentrated and purified by silica gel chromatography, eluting with 30-100% EtOAc in hexanes, to give the expected product as yellow solid (108 mg, 14% yield). LCMS: (M+H)+=330.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.83 (1H, s), 8.24 (1H, d, J=2.26 Hz), 8.07 (1H, dd, J=8.41, 1.88 Hz), 7.61 (1 H, d, J=8.53 Hz), 3.69 (2H, d, J=4.02 Hz), 3.61 (2H, br. s.), 3.57 (2H, d, J=4.27 Hz), 3.16-3.22 (2H, m), 3.10 (3H, s).

Aufarbeitung

  1. customthe pyridine solvent was evaporated under reduced pressure
  2. customThe resulting brown oil was triturated with hot CH2Cl2
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 30-100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c0fe81b619874200aa934a5a47c5ead1
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586751B2

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