Carbon Dioxide → HCID 69225377, compound

HRID 2113899Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[F:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([NH:36]O)=[NH:35])=[CH:32][CH:31]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]2[O:9][N:36]=[C:34]([C:33]3[CH:38]=[CH:39][C:30]([F:29])=[CH:31][CH:32]=3)[N:35]=2)[CH:5]=1

Participants

Conditions

Temperature: 115 °C

Procedure

In a 50 ml flask, 1.17 g (6.5 mmol) of isophtalic acid monomethyl ester are dissolved in 10 ml of DMF. To this solution, 1.16 g (7.2 mmol, 1.1 eq.) of 1,1′-carbonyl-diimidazole is added at room temperature under nitrogen. The mixture is stirred until carbon dioxide formation stops. Then, 1.00 g (6.5 mmol) of 4-fluoro-N-hydroxy-benzamidine is added and the resulting yellow solution stirred for 2 h. Now, another 1.16 g (7.2 mmol, 1.1 eq.) of 1,1′-carbonyl-diimidazole are added and the mixture is heated to 115° C. After 2 h at this temperature, the reaction mixture is cooled to room temperature and the solvent removed in vacuo. After chromatographical purification (160 g SiO2;eluent: hexane/CH2Cl2 6:4 to 1:1) the title compound is obtained as a white solid. Mass spectrum: m/z (M+H)+: 299.0

Workup

waitAfter 2 h at this temperature
temperaturethe reaction mixture is cooled to room temperature
customthe solvent removed in vacuo
customAfter chromatographical purification (160 g SiO2;eluent: hexane/CH2Cl2 6:4 to 1:1) the title compound
customis obtained as a white solid

Sources & evidence

ORD record: ord-f440c66072ab472daa7df265c0d004b7
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432293B2

Reaction notes

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