1,2-Dichloroethane → HCID 135407827, compound

HRID 1947214Notes

Reaction equation

COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[C:8]([CH:15]([CH3:17])[CH3:16])=[CH:7][C:6]=1[C:18]1[N:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=2)[C:20](=[O:23])[NH:21][N:22]=1.ClCCCl>CCCCCC>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[C:8]([CH:15]([CH3:17])[CH3:16])=[CH:7][C:6]=1[C:18]1[N:19]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:20](=[O:23])[NH:21][N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Crystals (3.30 g, 7.68 mmol) of 5-(2,4-bis(methoxymethoxy)-5-isopropyl phenyl)-4-(4-methoxyphenyl)-4H-[1,2,4]triazol-3-one (F60-03: an intermediate of Example 2-7) was added to a suspension of tribromoborane dimethylsulfide complex (11.65 g, 37.26 mol) and 1,2-dichloroethane (250 mL) in 300 mL eggplant shaped flask and stirred at room temperature for 2 hours and further at an external temperature of 80° C. for 24 hours. After completing the reaction, the reaction mixture was returned to room temperature and mixed with n-hexane (250 mL). The precipitates were collected by filtration, washed with diethyl ether and then purified by DIAION HP-20 column chromatography (water-methanol gradient elution), followed by CHP-20 column chromatography (water-methanol gradient elution) to obtain the title compound (OH-all: 370 mg, 14.8%). The fractions which were not sufficiently separated and purified were purified by HPLC fractionation to obtain the title compound (OH-all: 300 mg, total 670 mg, 26.8%).

Workup

customthe reaction
customwas returned to room temperature
filtrationThe precipitates were collected by filtration
washwashed with diethyl ether
custompurified by DIAION HP-20 column chromatography (water-methanol gradient elution)
washfollowed by CHP-20 column chromatography (water-methanol gradient elution)

Sources & evidence

ORD record: ord-5859ba33c46845a793ccbea1f0871c38
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399464B2

Reaction notes

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