Sodium hydride → 2,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-3-(2-methoxy-ethy)-4-methyl-3H-thiazol-2-ylidene]-amide

HRID 1037846

Reaktionsgleichung

Reaktionsgleichung von HRID 1037846
[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8]([CH:10]2[C:12]([CH3:14])([CH3:13])[C:11]2([CH3:16])[CH3:15])=[O:9])=[N:4][C:3]=1[CH3:17].[H-].[Na+].[CH3:20][O:21][CH2:22][CH2:23]Br>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[S:6][C:5](=[N:7][C:8]([CH:10]2[C:11]([CH3:16])([CH3:15])[C:12]2([CH3:13])[CH3:14])=[O:9])[N:4]([CH2:23][CH2:22][O:21][CH3:20])[C:3]=1[CH3:17]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 866189062,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-4-methyl-thiazol-2-yl)-amide

Produkt 1

HCID 686214272,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-3-(2-methoxy-ethy)-4-methyl-3H-thiazol-2-ylidene]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of the product of Example 118A (150 mg, 0.55 mmol), NaH (60% dispersion in mineral oil, 29.0 mg, 0.71 mmol) and 2-bromoethyl methyl ether (57 μl, 0.61 mmol) in 20 mL of 2:1 THF/DMF was processed according to the method desribed in Example 112B to provide the title compound: 1H NMR (300 MHz, DMSO-d6) δ 1.18 (s, 6H) 1.23 (s, 6H) 1.50 (s, 1H) 2.29 (s, 3H) 3.25 (s, 3H) 3.63 (t, J=5.3 Hz, 2H) 4.27 (t, J=5.3 Hz, 2H); MS (DCI/NH3) m/z 331 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-85628bfb342643abb4b54f6b62cdc4e3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546583B2

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