Sodium Hydroxide → HCID 86665541, compound

HRID 1770742Notes

Reaction equation

HRID 1770742 reaction equation
C(=O)([S:3][CH2:4][CH2:5][N:6]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7]1=[O:13])C.[OH-].[Na+]>CO.O>[SH:3][CH2:4][CH2:5][N:6]1[CH2:10][C:9]([CH3:11])([CH3:12])[NH:8][C:7]1=[O:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 87941945HCID 87941945, compound

Product 1

HCID 86665541HCID 86665541, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a cold (0° C.) solution of S-(2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)ethyl) ethanethioate (1.5 g, 6.9 mmol) in 14 mL of methanol and 7.2 mL of water was added 2.1 mL of 5 N NaOH. The external ice bath was removed and the mixture was allowed to warm to room temperature and stirred for 18 hours. Concentrated HCl (11 mL) was added and the resultant solution was concentrated to about ½ its original volume and extracted with ethyl acetate. The organic layer was washed with a brine solution, dried over sodium sulfate, and concentrated to give 1.2 g of a tan liquid. 1H NMR (CDCl3, 400 MHz) δ 1.32 (s, 6H), 1.39-1.43 (t, J=8.1 Hz, 1H) 2.66-2.27 (q, J=6.8 Hz, 2H), 3.24 (s, 2H), 3.36-3.340 (t, J=7.2 Hz, 2H), 4.94 (br s, 1H); LRMS (ESI/APCI) m/z 175 [M+H]+.

Workup

  1. customThe external ice bath was removed
  2. additionConcentrated HCl (11 mL) was added
  3. concentrationthe resultant solution was concentrated
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef051c7e3cb54d4cb984d0e32bb52f06
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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