Thionyl Chloride → HCID 23112900, compound

HRID 1180519Notes

Reaction equation

HRID 1180519 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([N:13]2[C:21]3[CH2:20][CH2:19][CH2:18][CH:17]([CH2:22][CH2:23]O)[C:16]=3[CH:15]=[N:14]2)[CH:9]=[CH:10][C:11]=1[Cl:12]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:3][CH2:23][CH2:22][CH:17]1[CH2:18][CH2:19][CH2:20][C:21]2[N:13]([C:8]3[CH:9]=[CH:10][C:11]([Cl:12])=[C:6]([Cl:5])[CH:7]=3)[N:14]=[CH:15][C:16]1=2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 23112892HCID 23112892, compound

Product 1

HCID 23112900HCID 23112900, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Thionyl cloride (4 mL) is slowly added at room temperature over a solution of 2-(1-(3,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)ethanol (512 mg, 1.65 mmol) in 20 mL of toluene. The reaction mixture is heated at 90° C. during 2 hours. The solvent is eliminated at reduced pressure. The crude is diluted in ethyl acetate and washed twice with a NaHCO3 solution. The solvent is next evaporated at reduced pressure to obtain 4-(2-chloroethyl)-4,5,6,7-tetrahydro-1-(3,4-dichlorophenyl)-1H-indazole (462 mg, 1.40 mmol, 85%, oil).

Workup

  1. washwashed twice with a NaHCO3 solution
  2. customThe solvent is next evaporated at reduced pressure

Sources & evidence

ORD record
ord-318189be2dce4c77952d511849eccaf1
Source dataset
uspto-grants-2007_10
Patent number
US07282499B2

Reaction notes

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