Dimethyl Sulfoxide → HCID 54457115, compound

HRID 365058Notes

Reaction equation

[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[C:15]([OH:17])[C:14]([Cl:18])=[CH:13][C:12]=2[F:19])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.[OH-].[K+].CS(C)=O.[Cl:26][CH:27]=[CH:28][CH:29](Cl)C>O>[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[C:15]([O:17][CH2:29][CH:28]=[CH:27][Cl:26])[C:14]([Cl:18])=[CH:13][C:12]=2[F:19])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

Conditions

Temperature: 100 °C

Procedure

3-Chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole (1 g) was suspended in a solution of potassium hydroxide (0.84 g) in water (8 ml). Dimethylsulfoxide (21 ml) was added to the suspension to make a uniform solution. To the resultant solution, 1,3-dichloro-1-butene (1.26 g) was added, and the mixture was stirred at 100° C. for 4 hours. After being allowed to cool, water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by silica gel thin chromatography using a mixture of ether and hexane (1:3) as an eluent to give 3-chloro-2-[4-chloro-2-fluoro-5-(3-chloro-2-propenyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole (0.65 g) (Compound No. 2). M.P., 68.5°-70.5° C.

Workup

temperatureto cool
extractionwas then extracted with ethyl acetate
washThe organic layer was washed with water
customdried
concentrationconcentrated
customThe residue was purified by silica gel thin chromatography
additiona mixture of ether and hexane (1:3) as an eluent

Sources & evidence

ORD record: ord-dc612e9fa059485689c5ab9a0be8bc02
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04608080

Reaction notes

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