Thionyl Chloride → HCID 14881122, compound

HRID 1608331Notes

Reaction equation

HRID 1608331 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][N:8]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:23]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][CH2:7][N:8]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14881121HCID 14881121, compound

Product 1

HCID 14881122HCID 14881122, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thionylchloride (0.42 ml, 6.0 mM) was added dropwise under ice-cooling to a compound 112 (1.29 g, 5 mM) dissolved in chloroform (6 ml), and stirred at room temperature for 5 hours. Chloroform (70 ml) was added to the reaction mixture, which mixture was then washed with dilute aqueous K2CO3, the resulting aqueous layer being twice extracted with further chloroform. The chloroform layer was combined, dried with anhydrous magnesium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 25 g), packed with chloroform, and eluted with chloroform to obtain compound 613 (1.00 g, yield: 87.5%).

Workup

  1. washwas then washed with dilute aqueous K2CO3
  2. extractionthe resulting aqueous layer being twice extracted with further chloroform
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionThe residue was charged on a column of silica-gel (C-200, 25 g)
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-f24649542e334099b48a2585b23682ce
Source dataset
uspto-grants-1989_09
Patent number
US04870176

Reaction notes

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