1-Butanol → n-Butyl 1-(4-iodophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate

HRID 67258Notes

Reaction equation

[CH2:1](O)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[I:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:22]([CH3:23])=[CH:21][C:20](=[O:24])[C:19]([C:25]([OH:27])=[O:26])=[N:18]2)=[CH:13][CH:12]=1>CCCCCC>[I:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:22]([CH3:23])=[CH:21][C:20](=[O:24])[C:19]([C:25]([O:27][CH2:1][CH2:2][CH2:3][CH3:4])=[O:26])=[N:18]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 50 ml of n-butanol, cooled to -5° C., there is added dropwise 2.62 g (0.022 mol) of thionyl chloride. The solution is stirred at 0° C. for 15 minutes and to it there is added 7.12 g (0.02 mol) of 1-(4-iodophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylic acid. (See Example 3). The suspension formed is stirred at room temperature for 3 days and to it there is added 150 ml of hexane. The suspension is stirred at room temperature for 2 days and is vacuum filtered. The filter cake (HCl salt of the desired product) is air dried and slurried in 150 ml of water for 3 hrs. The suspension is vacuum filtered to afford 4.25 g (52% yield) of product, mp 134°-137° C.

Workup

customThe suspension formed
stirringis stirred at room temperature for 3 days and to it there
stirringThe suspension is stirred at room temperature for 2 days
filtrationfiltered
customdried
waitslurried in 150 ml of water for 3 hrs
filtrationfiltered

Sources & evidence

ORD record: ord-44d5b9240df544318983c451e0d1e470
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04345934

Reaction notes

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