Thionyl Chloride → HCID 19027948, compound

HRID 1781277Notes

Reaction equation

HRID 1781277 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. customThe solvent and excess thionyl chloride were removed at reduced pressure
  3. customThe crude hydrochloride salt was then used directly in the next step without further purification

Sources & evidence

ORD record
ord-56b9447d44f64098b2f16a6ad9eaa5d8
Source dataset
uspto-grants-1997_05
Patent number
US05633258

Reaction notes

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