Chloromethyl methyl sulfide → HCID 15764851, compound

HRID 1656361Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[NH:5][C:6]=1[Br:7].CC(C)([O-])C.[K+].[CH3:26][S:27][CH2:28]Cl>O1CCCC1.O.CCOCC>[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:10][CH:9]=2)[N:5]([CH2:26][S:27][CH3:28])[C:6]=1[Br:7]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4,5-dibromo-2-(α,α,α-trifluoro-p-tolyl)pyrrole-3-carbonitrile (0.56 g, 1.42 mmol) in dry tetrahydrofuran, under nitrogen, is treated portion-wise with potassium t-butoxide (0.21 g, 1.81 mmol), stirred at 25° C. for 3/4 hour, treated dropwise with chloromethyl methyl thioether (0.18 g, 1.81 mmol), stirred at room temperature for 16 hours, heated at 49°-60° C. until reaction is complete by thin layer chromatography. The reaction mixture is diluted with water and ether. The phases are separated and the organic layer is dried over MgSO4 and concentrated in vacuo to give a black oil residue. The residue is flash chromatographed (silica/ 100:100:1 ether:petroleum ether:ethyl acetate) to give the title product as a red solid, mp 140°-145° C., identified by H1NMR and mass spectral analyses.

Workup

stirringstirred at room temperature for 16 hours
temperatureheated at 49°-60° C. until reaction
customThe phases are separated
dry with materialthe organic layer is dried over MgSO4
concentrationconcentrated in vacuo
customto give a black oil residue
customchromatographed (silica/ 100:100:1 ether:petroleum ether:ethyl acetate)

Sources & evidence

ORD record: ord-ec580a1a6298410f94eeec14ed01a94c
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254559

Reaction notes

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