Thionyl Chloride → HCID 19027948, compound

HRID 1780778Notes

Reaction equation

HRID 1780778 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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=[C:9]([CH2:26]O)[N:8]=1)([OH:3])=[O:2].S(Cl)([Cl:30])=O>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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=[C:9]([CH2:26][Cl:30])[N:8]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19027938HCID 19027938, compound

Product 1

HCID 19027948HCID 19027948, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(E-2-Carboxymethylethenyl)-3-dodecyloxy-6-(hydroxymethyl)pyridine (250 mg, 0.662 mmol) was dissolved in dry toluene (10 mL) under an argon atmosphere and cooled to 0∞C. Thionyl chloride (0.50 mL, 6.85 mmol) was slowly added and the solution was stirred at 0∞C for 30 minutes followed by 1 h at room temperature. The solvent and excess thionyl chloride were removed at reduced pressure. The crude hydrochloride salt was then used directly in the next step without further purification.

Workup

  1. temperaturecooled to 0∞C
  2. waitfollowed by 1 h at room temperature
  3. customThe solvent and excess thionyl chloride were removed at reduced pressure
  4. customThe crude hydrochloride salt was then used directly in the next step without further purification

Sources & evidence

ORD record
ord-acb63839ed254e6a8aed9cc1fae732f3
Source dataset
uspto-grants-1997_05
Patent number
US05631262

Reaction notes

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