Thionyl Chloride → HCID 14881118, compound

HRID 2352609Notes

Reaction equation

HRID 2352609 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]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]1=[O:22]>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]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]1=[O:22]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14881117HCID 14881117, compound

Product 1

HCID 14881118HCID 14881118, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thionylchloride (0.42 ml, 6.0 mM) was added dropwise under ice-cooling to compound 109 (1.22 g, 50 mM) dissolved in chloroform (10 ml), and stirred at room temperature for 3 hours. Chloroform was added to the reaction mixture, whereafter the mixture was washed with dilute aqueous K2CO3 and the resultant aqueous layer 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), and eluted with chloroform to obtain compound 612 (0.59 g, yield: 42.7%).

Workup

  1. washwas washed with dilute aqueous K2CO3
  2. extractionthe resultant aqueous layer 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-fe86b85ec8de464b855f4b5bfde4b3a4
Source dataset
uspto-grants-1989_10
Patent number
US04877877

Reaction notes

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