HCID 12138223, compound → 4-acetylsulfanylmethyl-3,5-dinitrobenzyl alcohol

HRID 2414922Notes

Reaction equation

Br[CH2:2][C:3]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].[C:17]([O-:20])(=[S:19])[CH3:18].[K+]>C(O)C>[C:17]([S:19][CH2:2][C:3]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15])(=[O:20])[CH3:18]

Participants

Conditions

Temperature: 150 °C

Procedure

4-bromomethyl-3,5-dinitro benzyl alcohol(800 mg, 2.75 mmol), anhydrous ethanol(10 ml) and potassium thioacetate(380 mg, 3.3 mmol) were charged into a 200 ml 2-neck round bottom flask equipped with condenser, dropping funnel and stirrer and put in an oil bath maintaining 150° C. and having thermocouple. The resulting mixture solution was heated at 100° C. for 30 minutes and cooled to ambient temperature. White solid formed during the reaction was filtered away and the filterate was concentrated by removing the solvent under reduced temperature. Pale yellow solid of 4-acetylsulfanylmethyl-3,5-dinitrobenzyl alcohol (710 mg, 2.48 mmol, yield 90%) was obtained by purification on a silica gel chromatography using 20% ethylacetate-hexane solvent system. Nuclear magnetic resonance (NMR) spectrum showed that the product has identical structure with compound V and the NMR data was set forth below.

Workup

customequipped with condenser
customput in an oil bath
temperatureThe resulting mixture solution was heated at 100° C. for 30 minutes
temperaturecooled to ambient temperature
customWhite solid formed during the reaction
filtrationwas filtered away
concentrationthe filterate was concentrated
customby removing the solvent under reduced temperature

Sources & evidence

ORD record: ord-35fe036298184f928a0aced8eea77a3d
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06815567B2

Reaction notes

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