Allyl Isothiocyanate → HCID 178456615, compound

HRID 1266193Notes

Reaction equation

HRID 1266193 reaction equation
[H-].[Na+].[NH2:3]/[C:4](/[C:11]([F:14])([F:13])[F:12])=[CH:5]\[C:6]([O:8]CC)=O.[CH2:15]([N:18]=[C:19]=[S:20])[CH:16]=[CH2:17]>CN(C=O)C>[CH2:15]([N:18]1[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[N:3]=[C:19]1[SH:20])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 5971Allyl IsothiocyanateHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonate

Product 1

HCID 178456615HCID 178456615, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 2.71 q, 60.0 mmol) was added to DMF (40 ml) solution of ethyl 3-amino-4,4,4-trifluorocrotonate spending 30 minutes under ice-cooling, followed by stirring for 20 minutes. Next, allyl isothiocyanate (5.3 ml, 54.0 mmol) was added under ice-cooling, followed by overnight stirring while gradually returning to room temperature. After completion of the reaction, the reaction solution was concentrated under a reduced pressure, water (40 ml) and 2 N hydrochloric acid (1.25 ml) were added to the thus obtained residue. The thus precipitated solid was isolated by filtration, washed with water and hexane and then thoroughly dried to obtain light yellow solid of 3-allyl-2-mercapto-6-trifluoromethyl-4(3H)-pyrimidinone (12.7 g, 89%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitfollowed by overnight
  4. stirringstirring
  5. customwhile gradually returning to room temperature
  6. customAfter completion of the reaction
  7. concentrationthe reaction solution was concentrated under a reduced pressure, water (40 ml) and 2 N hydrochloric acid (1.25 ml)
  8. additionwere added to the thus obtained residue
  9. customThe thus precipitated solid was isolated by filtration
  10. washwashed with water and hexane
  11. customthoroughly dried

Sources & evidence

ORD record
ord-0daf0e1f4bc440bd82d546bc2503e479
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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