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Water → 5-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]N,N-dimethylpyridine-2-carboxamide

HRID 1499682
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1499682
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C)C=O.[Cl:15][C:16]1[C:17]([CH3:38])=[C:18]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([N:35]([CH3:37])[CH3:36])=[O:34])=[N:31][CH:32]=2)[C:19]([O:25][CH3:26])=[C:20]([CH:22](O)[CH3:23])[CH:21]=1.O>ClCCl>[Cl:15][C:16]1[C:17]([CH3:38])=[C:18]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([N:35]([CH3:37])[CH3:36])=[O:34])=[N:31][CH:32]=2)[C:19]([O:25][CH3:26])=[C:20]([CH:22]([Cl:3])[CH3:23])[CH:21]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 866776335-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]-N,N-dimethylpyridine-2-carboxamide

Produkt 1

HCID 866776325-[3-chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]N,N-dimethylpyridine-2-carboxamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Cyanuric chloride (85 mg, 0.46 mmol) was added to N,N-dimethylformamide (0.036 mL, 0.46 mmol) at room temperature. After the formation of a white solid (10 minutes), methylene chloride (2 mL) was added, followed by 5-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]-N,N-dimethylpyridine-2-carboxamide (115 mg, 0.330 mmol, from Example 11, step 3). After the addition, the mixture was stirred at room temperature overnight. Water was added, and then diluted with dichloromethane. The organic phase was washed with sat. NaHCO3 solution, water and brine, then dried over MgSO4, concentrated. The residue was purified on silica gel (eluting with 0 to 80% EtOAc in hexanes) to give the desired product (76 mg, 63%). LCMS calculated for C18H21Cl2N2O2 (M+H)+: m/z=367.1; Found: 367.0.

Aufarbeitung

  1. additionAfter the addition
  2. washThe organic phase was washed with sat. NaHCO3 solution, water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (eluting with 0 to 80% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d80c728d9abb494c834f2acbbb5d4c57
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09199982B2

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