Thionyl Chloride → 1-[4-(2-Chloroethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole

HRID 891078Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[N:4]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21]O)=[CH:16][CH:15]=2)[N:3]=1.S(Cl)([Cl:25])=O>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:25][CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([N:4]2[C:5]([CH3:13])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:2]([CH3:1])=[N:3]2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethanol (step 1 of Example 2, 100 mg, 0.34 mmol) in toluene (3 mL) and chloroform (1 mL) was added thionyl chloride (50 μL, 0.68 mmol), and the resulting mixture was stirred at 80° C. for 3h. The reaction mixture was quenched by 2 M NaOH aq. and extracted with dichloromethane. Organic layer was dried (Na2SO4) and the solvent was evaporated to give the title compound as brown solids (quant.): MS (ESI) m/z 311 [M+H]+, 1H-NMR (CDCl3) δ 7.46-7.31 (9H, m), 3.74 (2H, t, J=7.3 Hz), 3.12 (2H, t, J=7.3 Hz), 2.34 (3H, s), 2.30 (3H, s).

Workup

customThe reaction mixture was quenched by 2 M NaOH aq.
extractionextracted with dichloromethane
dry with materialOrganic layer was dried (Na2SO4)
customthe solvent was evaporated

Sources & evidence

ORD record: ord-79962eed5bcb45a598321587c0c80dae
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001917B2

Reaction notes

Loading…