Methyl iodide → HCID 18519604, compound

HRID 1368024Notes

Reaction equation

HRID 1368024 reaction equation
[H-].[Na+].[NH2:3]/[C:4](/[C:11]([F:14])([F:13])[F:12])=[CH:5]\[C:6]([O:8]CC)=O.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([N:26]=[C:27]=[O:28])=[CH:18][CH:17]=1.[CH3:29]I>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([N:26]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[N:3]([CH3:29])[C:27]2=[O:28])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 18519615HCID 18519615, compound

Product 1

HCID 18519604HCID 18519604, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

Step 2 To a suspension of sodium hydride (1.23 g) in N,N-dimethylformamide (70 ml) was added dropwise a solution of ethyl 3-amino4,4,4-trifluorocrotonate (5.6 g) in toluene (50 ml) at 0° C. under nitrogen atmosphere. After 30 minutes, a solution of 4-chloronaphthyl isocyanate (28 mmol) in a mixed solvent of N,N-dimethylformamide (30 ml) and toluene (50 ml) was added dropwise at same temperature. The resulting solution was stirred for 2 hours at ambient temperature, and then methyl iodide (8 g) was added. After 12 hours, the reaction mixture was partitioned with water(200 ml) and a mixed solvent of ethyl acetate-hexane (1:1, 300 ml). The organic phase was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and obtained solid was washed with hot ethyl acetate to give 3-(4-chloronaphthalen-1-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindione (6.6 g) as a brown solid.

Workup

  1. waitAfter 12 hours
  2. customthe reaction mixture was partitioned with water(200 ml)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customobtained solid
  7. washwas washed with hot ethyl acetate

Sources & evidence

ORD record
ord-03f3a035b01e4b08beb70acfd973c59f
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

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