Thiomorpholine → HCID 19373203, compound

HRID 257111Notes

Reaction equation

HRID 257111 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[Cl-].[C:8]([O:14][CH3:15])(=[O:13])[CH2:9][C:10]([O-])=[O:11]>C(Cl)Cl>[O:11]=[C:10]([N:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1)[CH2:9][C:8]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 21193914HCID 21193914, compound

Product 1

HCID 19373203HCID 19373203, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20.6 g of thiomorpholine were added dropwise to a solution of 13.6 g of methyl malonate monochloride in 100 ml of methylene chloride. After stirring the mixture was diluted with 200 ml of methylene chloride, washed with water in a separating funnel, then dried, filtered and evaporated. The residue was purified by chromatography on silica gel with methylene chloride and then methylene chloride/acetone (1:1). There were obtained 17.6 g of methyl tetrahydro-b-oxo-4H-1,4-thiazine-4-propionate.

Workup

  1. washwashed with water in a separating funnel
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel with methylene chloride

Sources & evidence

ORD record
ord-f2ac6837f4f443ce9b2eb15053c34640
Source dataset
uspto-grants-1993_11
Patent number
US05260310

Reaction notes

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