HCID 18401472, compound → HCID 18401479, compound

HRID 1018448Notes

Reaction equation

HRID 1018448 reaction equation
Cl[CH2:2][N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH3:10])[C:5](=[O:11])[C:4]1=[O:12].[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>>[C:13]([S:15][CH2:2][N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH3:10])[C:5](=[O:11])[C:4]1=[O:12])(=[O:16])[CH3:14]

Participants

3

Reactant 2

HCID 18401472HCID 18401472, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 18401479HCID 18401479, compoundYield 44%

Conditions

Temperature
0 °C

Procedure

To a solution of crude 1-(chloromethyl)-4-ethyl-piperazine-2,3-dione (170 mg, 0.9 mmol) in CDCl3 (1 ml) solid potassium thioacetate (123 mg, 1.08 mmol) was added with stirring at 0° C. The reaction mixxture was allowed to stir at room temperature overnight. The mixture was centifuged and the supernatant solution collected. The residual solid (KCl) was washed with CDCl3 (2 ml) and the organic solutions combined and the solvent removed in vacuo. The residue was chromatographed on silica gel (6 g, 63-200 μm) using chloroform-methanol (19:1) to give 1-(acetylthiomethyl)-4- ethyl-piperazine-2,3-dione as a white solid (overall yield 44%). NMR-specrum in CDCl3: 1.22 (t, 3H, J=7 Hz), 2.44 (s, 3H), 3.48 (q, 2H, J=7 Hz), 3.4-3.7 (m, 4H), 4.95 (s, 2H) ppm.

Workup

  1. stirringto stir at room temperature overnight
  2. customthe supernatant solution collected
  3. washThe residual solid (KCl) was washed with CDCl3 (2 ml)
  4. customthe solvent removed in vacuo
  5. customThe residue was chromatographed on silica gel (6 g, 63-200 μm)

Sources & evidence

ORD record
ord-e2c9cd0f3cf34bb69f603d598dd5b7c0
Source dataset
uspto-grants-2002_11
Patent number
US06482818B2

Reaction notes

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