Sodium Iodide → HCID 69139206, compound

HRID 895700Notes

Reaction equation

HRID 895700 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[S:6].Br[CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:13]([O:12][C:10](=[O:11])[C:9](=[O:15])[CH2:8][S:6][C:2]1[NH:1][CH2:5][CH2:4][N:3]=1)[CH3:14]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 66144Ethyl bromopyruvateHCID 2723650Ethylenethiourea

Product 1

HCID 69139206HCID 69139206, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2-imidazolidinethione (1.02 g, 10 mmol), ethyl 3-bromopyruvate (1.95 g, 10 mmol), potassium carbonate (1.38 g, 10 mmol), sodium iodide (10 mg), Adogen (200 mg) in N,N-dimethyl formamide (15 mL) was stirred at 20° C. for 15 hours under nitrogen. The reaction mixture was diluted with water and then extracted ethyl acetate. Organic phase was dried over sodium sulfate, evaporated, and chromatographed (silica gel, dichloromethane-methanol 9:1), giving the expected product, 3-(4,5-dihydro-1H-imidazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester, as a brown solid (1.8 g, 83%). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 4.36 (d, J=7.1 Hz, 2H), 4.25-4.00 (m, 3H), 3.57 (d, J=11.2 Hz, 1H), 3.50-3.35 (m 1H), 3.25-3.10 (m, 1H), 1.37 (t, J=7.1 Hz, 3H).

Workup

  1. dry with materialOrganic phase was dried over sodium sulfate
  2. customevaporated
  3. customchromatographed (silica gel, dichloromethane-methanol 9:1)

Sources & evidence

ORD record
ord-57b1f8de204b46a29a27bceb87b874e5
Source dataset
uspto-grants-2005_07
Patent number
US06916850B2

Reaction notes

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