Hydrochloric Acid → HCID 10116093, compound

HRID 1247554Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([C:8]([CH3:20])([CH3:19])[CH2:9][C:10]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:11]([OH:13])=O)[CH:7]=1.S(Cl)(Cl)=O.[NH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:34](=[O:35])[O:33][CH2:32]2.Cl>CC(N(C)C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([C:8]([CH3:19])([CH3:20])[CH2:9][C:10]([OH:18])([C:14]([F:15])([F:17])[F:16])[C:11]([NH:28][C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[C:34](=[O:35])[O:33][CH2:32]3)=[O:13])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

255 mg of 4-(5-fluoro-2-nitrophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleric acid in 3 ml of dimethyl acetamide is mixed at 0° C. with 0.105 ml of thionyl chloride, stirred for 30 minutes at 0° C. and 45 minutes at room temperature and combined with 300 mg of 5-aminophthalide. After 16 hours at room temperature, it is mixed with 2 M hydrochloric acid and ethyl acetate, the organic phase is washed neutral with water, dried (Na2SO4) and concentrated by evaporation. After chromatography on silica gel with hexane-ethyl acetate (3:2) and recrystallization from diisopropyl ether, 80 mg of 5-[4-(5-fluoro-2-nitrophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]phthalide is obtained, flash point 200–201° C.

Workup

waitAfter 16 hours at room temperature
washthe organic phase is washed neutral with water
dry with materialdried (Na2SO4)
concentrationconcentrated by evaporation
customAfter chromatography on silica gel with hexane-ethyl acetate (3:2) and recrystallization from diisopropyl ether

Sources & evidence

ORD record: ord-3e8fd32cffaf4b21b659dc47fc265ea1
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129270B2

Reaction notes

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