Phenol → HCID 66751337, compound

HRID 2043356Notes

Reaction equation

[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][N:11]([CH3:31])[S:12]([N:15]1[CH:19]=[C:18]([CH2:20][N:21]([C:24]2[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=2)[CH2:22][CH3:23])[N:17]=[CH:16]1)(=[O:14])=[O:13]>CN(C)C=O>[CH3:10][N:11]([CH3:31])[S:12]([N:15]1[CH:19]=[C:18]([CH2:20][N:21]([CH2:22][CH3:23])[C:24]2[CH:29]=[CH:28][N:27]=[C:26]([O:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[N:25]=2)[N:17]=[CH:16]1)(=[O:13])=[O:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To sodium hydride (0.194 g, 55% in mineral oil, 4.4 mmol) in dimethylformamide (1.5 ml) was added phenol (0.418 g, 4.4 mmol) and stirring was continued for 15 min at room temperature. To this reaction mixture 4-{[(2-chloro-pyrimidin-4-yl)-ethyl-amino]-methyl}-imidazole-1-sulfonic acid dimethylamide (0.153 g, 0.44 mmol) was added. After stirring and heating to 80° C. overnight the solvent was evaporated. Water was added (5 ml) and the mixture was extracted with ethyl acetate (20 ml) twice. The combined organic layers were washed with water, dried over magnesium sulphate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: heptane/ethyl acetate=95:5) to yield the title compound as a colourless gum, MS (ISP): 403.4 ((M+H)+.).

Workup

stirringAfter stirring
customwas evaporated
additionWater was added (5 ml)
extractionthe mixture was extracted with ethyl acetate (20 ml) twice
washThe combined organic layers were washed with water
dry with materialdried over magnesium sulphate
customevaporated
customThe residue was purified

Sources & evidence

ORD record: ord-22c43e8e43004d21adcf0102654c7192
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586617B2

Reaction notes

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