Thionyl Chloride → HCID 15463549, compound

HRID 430471Notes

Reaction equation

[OH:1][C:2]([C:18]([F:21])([F:20])[F:19])([CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])([CH3:9])[CH3:8])[C:3]([OH:5])=O.S(Cl)(Cl)=O.[NH2:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:32](=[O:33])[O:31][CH2:30]2>CC(N(C)C)=O>[OH:1][C:2]([C:18]([F:21])([F:20])[F:19])([CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])([CH3:9])[CH3:8])[C:3]([NH:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:32](=[O:33])[O:31][CH2:30]2)=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

400 mg of 2-hydroxy-4-(2-methoxyphenyl)-4-methyl-2-trifluoromethyl-valeric acid is mixed in 5 ml of dimethylacetamide at 0° C. with 0.23 ml of thionyl chloride. After 30 minutes of stirring at 0° C., 390 mg of 5-aminophthalide in 2 ml of dimethylacetamide is added, and the mixture is stirred for another 4 hours at this temperature. Then, ice water is added, extracted with ethyl acetate, and after drying (Na2SO4), the crude product is chromatographed on silica gel. With hexane/ethyl acetate (50:50), the title compound is obtained in a crystalline state, flash point 134-135° C.

Workup

stirringthe mixture is stirred for another 4 hours at this temperature
extractionextracted with ethyl acetate
dry with materialafter drying (Na2SO4)
customthe crude product is chromatographed on silica gel

Sources & evidence

ORD record: ord-4bf377a5527d484ebf70cabc1bedacf9
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323199B1

Reaction notes

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