Thionyl Chloride → 2-(E-2-Carboxymethylethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-chloromethylpyridine hydrochloride

HRID 263409Notes

Reaction equation

HRID 263409 reaction equation
[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:11][CH:10]=[C:9]([CH2:26]O)[N:8]=1)([OH:3])=[O:2].O=S(Cl)[Cl:30]>C1(C)C=CC=CC=1>[ClH:30].[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:11][CH:10]=[C:9]([CH2:26][Cl:30])[N:8]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 196068302-(E-2-Carboxymethylethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-hydroxymethylpyridine

Product 1

HCID 196068312-(E-2-Carboxymethylethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-chloromethylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(E-2-Carboxymethylethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-hydroxymethylpyridine (1.00 g, 2.69 mmol) was added to a cooled (0° C.) solution of SOCl2 (1.96 mL, 26.9 mmol) in anhydrous toluene (20 mL) under an argon atmosphere. The cooling bath was removed and the reaction was stirred at room temperature for 4.5 h. The solvent and excess SOCl2 were evaporated. The resulting crude product (tan solid) was used without further purification. This material served as the starting material for the preparation of the compounds set out in the following examples.

Workup

  1. customThe cooling bath was removed
  2. customThe solvent and excess SOCl2 were evaporated
  3. customThe resulting crude product (tan solid) was used without further purification
  4. customThis material served as the starting material for the preparation of the compounds

Sources & evidence

ORD record
ord-f30a3e456baa4027aa47e61a5eb0abb1
Source dataset
uspto-grants-1997_07
Patent number
US05643914

Reaction notes

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