Thionyl Chloride → HCID 19831103, compound

HRID 1493232Notes

Reaction equation

HRID 1493232 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[CH:14](O)[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[CH:14]([Cl:24])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19831107HCID 19831107, compound

Product 1

HCID 19831103HCID 19831103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Starting from 3-chloro-4-pyridine carbonitrile, by reaction with 4-chlorobenzyl alcohol in the presence of sodium hydride in dimethylformamide, 3-(4-chlorobenzyloxy)-4-pyridine carbonitrile is obtained, which is reacted with butyllithium in diethyl ether to 3-(4-chlorobenzyloxy)-4-valeryl pyridine. The keto group of this 4-valeryl derivative is reduced with sodium boron hydride to the hydroxyl group; 1-[3-(4-chlorobenzyloxy)-4-pyridyl]-1-pentanol is obtained. The hydroxyl group of the pentanol derivative is exchanged with thionyl chloride in methylene chloride for a chlorine group, 3-(4-chlorobenzyloxy)-4-(1-chloropentyl)-pyridine is obtained. By subsequent reaction with imidazole in the presence of sodium hydride (analogously to example 13), the 3-(4-chlorobenzyloxy)-4-[1-(1-imidazolyl)-pentyl]-pyridine is obtained.

Sources & evidence

ORD record
ord-b45d7f40c791478b98e593e446351785
Source dataset
uspto-grants-1991_06
Patent number
US05021434

Reaction notes

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