3-(3-Chlorophenyl)-alpha-(4-phenyl-2-thiazolyl)-2,1-benzisoxazole-5-methanol → HCID 22048460, compound

HRID 1830803Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([CH:17]([C:19]4[S:20][CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[N:23]=4)[OH:18])=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1>O1CCOCC1.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([C:19]4[S:20][CH:21]=[C:22]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:23]=4)=[O:18])=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of intermediate (14) (0.0656 mol) and MnO2 (27.5 g) in 1,4-dioxane (275 ml) was stirred at 80° C. for 3 hours, then cooled to room temperature, filtered over celite and pasted up with CH2Cl2/CH3OH. The solvent was evaporated till dryness, yielding 27.3 g (100%) of [3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl](4-phenyl-2-thiazolyl)-methanone (intermediate 15).

Workup

temperaturecooled to room temperature
filtrationfiltered over celite
customThe solvent was evaporated till dryness

Sources & evidence

ORD record: ord-d72d3f3bb9c442be9700e0c7f5b3bb0b
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067531B2

Reaction notes

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