S-Ethylisothiourea → HCID 178477341, compound

HRID 2300823

Reaction equation

HRID 2300823 reaction equation
[OH-].[K+].[CH2:3]([S:5][C:6](=[NH:8])[NH2:7])[CH3:4].C([O:11][CH:12]=[C:13]([C:19]#[N:20])[C:14](OCC)=O)C>CO>[CH2:3]([S:5][C:6]1[N:7]=[C:12]([OH:11])[C:13]([C:19]#[N:20])=[CH:14][N:8]=1)[CH3:4]

Participants

5

Reactant 3

HCID 5139S-EthylisothioureaHCID 14797Potassium HydroxideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 178477341HCID 178477341, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of potassium hydroxide (640 mg, 10 mmol) in methanol (6 mL) at 0° C. was added 2-ethyl-2-thiopseudourea (1.85 g, 10 mmol). The mixture was warmed to room temperature, stirred for 5 min, then filtered off potassium bromide under N2. The filtrate was cooled down to 0° C. then ethyl (ethoxymethylene)cyanoacetate (420 mg, 2.5 mmol) was added. The mixture was gradually warmed to room temperature and stirred for 20 h. The solvent was removed under reduced pressure, and the crude material was purified by flash chromatography using 4% 2M NH3 in MeOH/CH2Cl2 system to obtain 288 mg of the title compound. Mass spectrum 181 (EI, M+).

Workup

  1. filtrationfiltered off potassium bromide under N2
  2. temperatureThe filtrate was cooled down to 0° C.
  3. temperatureThe mixture was gradually warmed to room temperature
  4. stirringstirred for 20 h
  5. customThe solvent was removed under reduced pressure
  6. customthe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-eba92fbec2954e5dbeea0bfa6f37264a
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Linked notes

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