Isoamyl Nitrite → HCID 22272859, compound

HRID 1064805Notes

Reaction equation

N(OCCC(C)C)=O.N[C:10]1[C:11]([CH:32]([CH3:34])[CH3:33])=[C:12]([NH:19][C:20](=[O:31])[CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]2)[C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:15]=1.[CH3:35][S:36]SC>>[CH:32]([C:11]1[C:10]([S:36][CH3:35])=[CH:15][CH:14]=[C:13]([CH:16]([CH3:17])[CH3:18])[C:12]=1[NH:19][C:20](=[O:31])[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]1)([CH3:34])[CH3:33]

Participants

Reactant 3

HCID 8053Isoamyl Nitrite

HCID 12232Dimethyl Disulfide

HCID 22272619HCID 22272619, compound

Product 1

HCID 22272859HCID 22272859, compoundYield 68%

Conditions

Temperature: 110 °C

Procedure

Isoamyl nitrite (1 ml) was slowly dropped into a solution of N-[3-amino-2,6-diisopropylphenyl]-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide (500 mg) in dimethyl disulfide (10 ml) with heating and stirring at 110° C. followed by stirring at the same temperature for 20 minutes. The reaction solution was allowed to cool and concentrated. The resulting residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=20:1) to provide 370 mg (yield 68%) of N-[2,6-diisopropyl-3-(methylthio)phenyl]-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide.

Workup

temperaturewith heating
stirringby stirring at the same temperature for 20 minutes
temperatureto cool
concentrationconcentrated
customThe resulting residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=20:1)

Sources & evidence

ORD record: ord-80c5c7046e084278b81c4ce44a730c83
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969711B2

Reaction notes

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