Ethyl isothiocyanate → HCID 178462983, compound

HRID 1266190Notes

Reaction equation

HRID 1266190 reaction equation
[H-].[Na+].[CH2:3]([N:5]=[C:6]=[S:7])[CH3:4].[NH2:8]/[C:9](/[C:16]([F:19])([F:18])[F:17])=[CH:10]\[C:11](OCC)=[O:12]>CN(C=O)C>[CH2:3]([N:5]1[C:11](=[O:12])[CH:10]=[C:9]([C:16]([F:19])([F:18])[F:17])[N:8]=[C:6]1[SH:7])[CH3:4]

Participants

5

Reactant 3

HCID 10966Ethyl isothiocyanateHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonate

Product 1

HCID 178462983HCID 178462983, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With stirring under ice-cooling, sodium hydride (60% in oil, 3.73 g, 56.0 mmol) and ethyl isothiocyanate (4.38 ml, 56.0 mmol) were added in that order to DMF (35 ml) solution of ethyl 3-amino-4,4,4-trifluorocrotonate, Followed by stirring overnight while gradually returning to room temperature. After completion of the reaction, the reaction solution was concentrated under a reduced pressure, water (20 ml) was added to the thus obtained residue, and then concentrated hydrochloric acid (15 ml) was added. The thus precipitated solid was isolated by filtration, washed with water (100 ml) and then thoroughly dried to obtain 3-ethyl-2-mercapto-6-trifluoromethyl-4-(3H)-pyrimidinone (11.0 g, 99%).

Workup

  1. temperaturecooling
  2. stirringby stirring overnight
  3. customwhile gradually returning to room temperature
  4. customAfter completion of the reaction
  5. concentrationthe reaction solution was concentrated under a reduced pressure, water (20 ml)
  6. additionwas added to the thus obtained residue
  7. additionconcentrated hydrochloric acid (15 ml) was added
  8. customThe thus precipitated solid was isolated by filtration
  9. washwashed with water (100 ml)
  10. customthoroughly dried

Sources & evidence

ORD record
ord-5b6250efe9924dbb8f0ff0e4d11bc9c0
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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