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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1037846Generated: October 26, 2026

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

https://huagongshe.com/reaction/1037846

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant2-Bromoethyl methyl etherHCID 80972—
Reactant2,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-4-methyl-thiazol-2-yl)-amideHCID 86618906—
Solventtetrahydrofuran N,N-dimethylformamideHCID 21974620—
Product2,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-3-(2-methoxy-ethy)-4-methyl-3H-thiazol-2-ylidene]-amideHCID 68621427—

Reaction Steps

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)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08546583B2
Source datasetuspto-grants-2013_10
ORD IDord-85628bfb342643abb4b54f6b62cdc4e3
Source noteuspto-grants-2013_10