Potassium Carbonate → 5-(4-chlorobenzylthio)pyridazin-3(2H)-one

HRID 2059860Notes

Reaction equation

HRID 2059860 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][SH:15])=[CH:10][CH:9]=1.I[C:17]1[CH:22]=[N:21][NH:20][C:19](=[O:23])[CH:18]=1>>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15][C:17]2[CH:22]=[N:21][NH:20][C:19](=[O:23])[CH:18]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 804094-Chlorobenzyl mercaptanHCID 166383305-Iodo-2,3-dihydropyridazin-3-one

Product 1

HCID 585798575-(4-chlorobenzylthio)pyridazin-3(2H)-oneYield 51.9%

Conditions

Temperature
100 °C

Procedure

A mixture of K2CO3 (65.4 mg, 0.47 mmol), (4-chlorophenyl)methanethiol (250 mg, 1.58 mmol), and 5-iodopyridazin-3(2H)-one (35 mg, 0.16 mmol) was stirred at 100° C. for 18 hours. After removal of the precipitate by filtration and concentration of the filtrate, the crude product was purified by prep-HPLC (C18 column/H2O:MeOH:TFA 90:10:0.1 to 10:90:0.1 gradient) to yield 5-(4-chlorobenzylthio)pyridazin-3(2H)-one 9A (21 mg, 51.6% yield). 1H NMR (400 MHz, Chloroform-D) δ ppm 11.08 (1H, br. s.), 7.57 (1H, d, J=2.01 Hz), 7.33 (4H, s), 6.57 (1H, d, J=2.01 Hz), 4.12 (2H, s).

Workup

  1. customAfter removal of the precipitate
  2. filtrationby filtration and concentration of the filtrate
  3. customthe crude product was purified by prep-HPLC (C18 column/H2O:MeOH:TFA 90:10:0.1 to 10:90:0.1 gradient)

Sources & evidence

ORD record
ord-d648ca5a762e43f194855d28c73cd3e3
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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