Water → HCID 80021658, compound

HRID 1770736Notes

Reaction equation

HRID 1770736 reaction equation
C(=O)([S:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[NH:8][C:7]1=[O:14])C.O.[OH-].[Na+]>CO>[SH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:12])([CH3:13])[NH:8][C:7]1=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59355190HCID 59355190, compound

Product 1

HCID 80021658HCID 80021658, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (0° C.) solution of S-(2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)ethyl) ethanethioate (17 g, 74 mmol) prepared as described in International Patent Publication Number WO 2010/054009 A1 (Jain et al., Apr. 11, 2009), in 150 mL of methanol and 100 mL of water was added 22.5 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 hydrochloric acid (8 mL) and 10 mL of water were added and the resultant solution was concentrated to about half of its original volume. White solid product precipitated out of solution and was collected on a glass fritted filter. The remaining aqueous solution was extracted with ethyl acetate, and the organic layer was then successively washed with water and sat. NaCl solutions. The organic fraction was dried over sodium sulfate and concentrated to a white solid, which was combined with the precipitated material to give the desired product (13.2 g, 70.2 mmol, 95%). 1H NMR (CDCl3, 400 MHz) δ 1.37-1.41 (t, J=8.5 Hz, 1H), 1.48 (s, 6H), 2.81-2.86 (m, 2H), 3.69-3.73 (t, J=7.0 Hz, 1H), 5.53 (br s, 1H); LRMS (ESI/APCI) m/z 189 [M+H]+.

Workup

  1. customThe external ice bath was removed
  2. additionConcentrated hydrochloric acid (8 mL) and 10 mL of water were added
  3. concentrationthe resultant solution was concentrated to about half of its original volume
  4. customWhite solid product precipitated out of solution
  5. customwas collected on a glass fritted filter
  6. extractionThe remaining aqueous solution was extracted with ethyl acetate
  7. washthe organic layer was then successively washed with water and sat. NaCl solutions
  8. dry with materialThe organic fraction was dried over sodium sulfate
  9. concentrationconcentrated to a white solid, which

Sources & evidence

ORD record
ord-b4b42eaa608745ca8ce4e865d9a93426
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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