Ethyl bromoacetate → HCID 20330525, compound

HRID 918566Notes

Reaction equation

HRID 918566 reaction equation
[H-].[Na+].[SH:3][CH2:4][C:5]1[CH:10]=[N:9][C:8]([CH3:11])=[C:7]2[O:12][C:13]([CH3:17])([CH3:16])[O:14][CH2:15][C:6]=12.[H][H].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[C:22]([CH2:21][S:3][CH2:4][C:5]1[CH:10]=[N:9][C:8]([CH3:11])=[C:7]2[O:12][C:13]([CH3:17])([CH3:16])[O:14][CH2:15][C:6]=12)([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 20330540HCID 20330540, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20330525HCID 20330525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 0.01 mole of sodium hydride in 50 ml. dry dimethylformamide under nitrogen at 0.5° is added dropwise a solution of 0.01 mole of 5-mercaptomethyl-2,2,8-trimethyl-4H-1,3-dioxino[4,5-C]pyridine in 10 ml. of dimethylformamide. When the evolution of hydrogen has ceased, 0.011 mole of ethyl bromoacetate is added. The reaction mixture is allowed to stir overnight at room temperature and then poured into a mixture of benzene-ice water. The organic layer is separated and washed well with water, dried and concentrated in vacuo. Chromatography on silica gel and elution with ether petroleum ether (10-75%) gives 5-carboethoxymethylthiomethyl-2,2,8-trimethyl-4H-1,3-dioxino[4,5-C]pyridine.

Workup

  1. customThe organic layer is separated
  2. washwashed well with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. washChromatography on silica gel and elution with ether petroleum ether (10-75%)

Sources & evidence

ORD record
ord-f446190cbd2846159f3ddab1220905c7
Source dataset
uspto-grants-1976_07
Patent number
US03971797

Reaction notes

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