Potassium Hydroxide → HCID 19041040, compound

HRID 1683796Notes

Reaction equation

[OH-:1].[K+].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]4[CH2:28][O:27]4)[N:21]=3)[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]>O.CS(C)=O>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([OH:1])[CH2:28][OH:27])[N:21]=3)[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 505 mg of potassium hydroxide dissolved in 30 ml of water was added to a solution of 700 mg of 2-(3,4-diethoxyphenyl)-4-(6-oxiranyl-2-pyridyl)thiazole dissolved in 30 ml of dimethyl sulfoxide. The mixture was stirred at 100° C. for 7 hours. The reaction mixture was subjected to extraction three times with 50 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=20/1) and then recrystallized from ethyl acetate-n-hexane to obtain 350 mg of 2-(3,4-diethoxyphenyl)-4-[6-(1,2-dihydroxyethyl)-2-pyridyl]-thiazole.

Workup

extractionThe reaction mixture was subjected to extraction three times with 50 ml of ethyl acetate
dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
customThe solvent was removed by distillation
customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=20/1)
customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record: ord-7f4ee7b0b9694fd19aa31157da2fffde
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639770

Reaction notes

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