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Dimethyl Sulfoxide → HCID 54457115, compound

HRID 365058
Notes
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Reaction equation

HRID 365058 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 1850782-Chloro-5-(3-chloro-4,5,6,7-tetrahydroindazol-2-yl)-4-fluorophenolHCID 538595701,3-Dichloro-but-1-ene

Product 1

HCID 54457115HCID 54457115, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

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

  1. temperatureto cool
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel thin chromatography
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes