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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 522573Generated: October 30, 2026

Methyl iodide → HCID 53363962, compound

https://huagongshe.com/reaction/522573

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactanttert-Butyl 4-(4-(3,4,5-trimethoxybenzoyl)thiazol-2-yl)benzylcarbamateHCID 53363957—
SolventDimethylformamideHCID 6228—
ProductHCID 53363962HCID 5336396261.3%

Reaction Steps

At 0° C., to a solution of compound 68a (100 mg, 0.2 mmol) in 5 mL DMF was added sodium hydride (10 mg, 0.2 mmol), then iodomethane (77 mg, 0.4 mmol) was added to the reaction mixture and stirred at RT overnight. The mixture was quenched with a sat. NaHCO3 solution, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 71a. Yield: 61.3%. 1H NMR (500 MHz, DMSO-d6) δ 8.30 (s, 1H), 8.02 (d, 2H, J=8.0 Hz), 7.82 (s, 2H), 7.36 (br, 2H), 4.50 (s, 2H), 4.00 (s, 3H), 3.98 (s, 6H), 2.90 (d, br, 3H), 1.50 (s, 9H). MS (ESI) m/z 521.2 (M+Na)+, 496.9 (M−H)−.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09334242B2
Source datasetuspto-grants-2016_05
ORD IDord-524716fec3d44250a3bb05f464b30a84
Source noteuspto-grants-2016_05