Potassium Carbonate → 1-(2-Chloroethyl)-3-benzyl-2-oxo-1,2,5,6,7,8-hexahydroquinoxaline

HRID 1608336Notes

Reaction equation

HRID 1608336 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][N:8]1[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[N:11]=[C:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][CH2:7][N:8]1[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[N:11]=[C:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 148813532-Hydroxyethyl-3-benzyl-2-oxo-1,2,5,6,7,8-hexahydroquinoxaline

Product 1

HCID 148813541-(2-Chloroethyl)-3-benzyl-2-oxo-1,2,5,6,7,8-hexahydroquinoxalineYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionylchloride (2.96 ml, 1.3 eq.) was added dropwise under ice-cooling to compound 643 (9.09 g, 32 mM) dissolved in chloroform (30 ml), and stirred at room temperature for 2 hours. Dilute aqueous K2CO3 was added to the reaction mixture, which mixture was then extracted twice with chloroform, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 100 g) packed with chloroform and eluted with chloroform to obtain compound 644 (7.55 g, yield: 78.0%).

Workup

  1. extractionwas then extracted twice with chloroform
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionThe residue was charged on a column of silica-gel (C-200, 100 g)
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-2831cb6d6a3442f18156474ac3a9b86a
Source dataset
uspto-grants-1989_09
Patent number
US04870176

Reaction notes

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