Sodium Methoxide → [2-Methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea

HRID 2222184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222184
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=[CH:15][C:14]=1[O:25][CH3:26])=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[CH3:26][O:25][C:14]1[CH:15]=[CH:16][C:17]([CH:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[CH:18][C:13]=1[NH:12][C:10]([NH2:9])=[S:11]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 227195711-Benzoyl-3-[2-methoxy-5-(tetrahydropyran-4-yl)-phenyl]-thiourea

Produkt 1

HCID 22015747[2-Methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thioureaAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 3.25 g (8.77 mmol) 1-benzoyl-3-[2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea in 45 ml methanol was added dropwise 0.25 ml (1.32 mmol) 5.3 M sodium methylate solution and stirring continued for 1 h at room temperature. The mixture was then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 1.90 g (81%) [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea as a white foam. ES-MS m/e (%): 267 (M+H+, 100).

Aufarbeitung

  1. additionThe mixture was then poured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-75df0a407656438696ef50b1d9af28b2
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371748B2

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