Dicyclohexylcarbodiimide → HCID 59850840, compound

HRID 2373121Notes

Reaction equation

[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:16]([OH:18])=[O:17].O[CH2:20][CH2:21][O:22][C:23](=[O:27])[C:24]([CH3:26])=[CH2:25].C1(C)C=CC(S(O)(=O)=O)=CC=1.CN(C)C1C=CN=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:23]([O:22][CH2:21][CH2:20][O:17][C:16]([C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13](=[O:15])[C:14]=2[CH:1]=1)=[O:18])(=[O:27])[C:24]([CH3:26])=[CH2:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of thioxanthen-9-one-2-carboxylic acid (3.8 g, 19.8 mmol), 2-hydroxyethylmethacrylate (7.7 g, 59.3mmol), 4-dimethylamino-pyridine p-toluenesulfonic acid salt (2.3 g, 7.9mmol), and anhydrous dichloromethane (31 mL) is cooled to 0° C. under nitrogen and treated with 1,3-dicyclohexyl-carbodiimide (2.1 g, 10.1 mmol). After 15 min, the reaction mixture was warmed to ambient and stirred for 12 h. The precipitated urea by product was filtered, and the filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine. The solution was dried (Na2SO4)and concentrated to deposit yellow oil. The product was purified by column chromatography to provide 500 mg of a pale yellow solid (17% of theory). 1H (CDCl3): δ 1.99 (s, 3H), 4.60 (dd, 4H), 5.60 (s, 1H), 6.20 (s, 1H), 7.60 (m, 4H), 8.20 (d, 1H), 8.70 (d, 1H), 9.30 (s, 1H).

Workup

temperaturethe reaction mixture was warmed to ambient and
filtrationThe precipitated urea by product was filtered
washthe filtrate was washed successively with 10% aqueous HCl, 10% aqueous NaHCO3, water, and brine
concentrationconcentrated
customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-06aad33500e0458a8ba915a7cea764d1
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459263B2

Reaction notes

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