Water → HCID 54270959, compound

HRID 1707568Notes

Reaction equation

HRID 1707568 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[C:10]([NH:14][C:15](OC)=[O:16])[C:11]([F:13])=[CH:12][C:7]=2[S:6][C:5]1=[O:19])([CH3:3])[CH3:2].[H-].[Na+].[NH2:22]/[C:23](/[C:30]([F:33])([F:32])[F:31])=[CH:24]\[C:25]([O:27]CC)=O.O>CN(C)C=O>[CH:1]([N:4]1[C:8]2[CH:9]=[C:10]([N:14]3[C:25](=[O:27])[CH:24]=[C:23]([C:30]([F:31])([F:32])[F:33])[NH:22][C:15]3=[O:16])[C:11]([F:13])=[CH:12][C:7]=2[S:6][C:5]1=[O:19])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 18961693HCID 18961693, compound

Product 1

HCID 54270959HCID 54270959, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-isopropyl-6-fluoro-5-methoxycarbonylamino -2(3H)-benzothiazolone (2.8 g) in N,N-dimethylformamide (10 g), sodium hydride (0.4 g) and ethyl 3-amino-4,4,4-trifluorocrotonate (0.9 g) were added, and the resultant mixture was heated under reflux for 3 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by column chromatography to give 1-[3-isopropyl-6-fluoro-2(3H) -benzothiazolon -5-yl]-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine -2,6-dione (0.8 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-12ca04a8f32f4fc38c36c6acdbd908b6
Source dataset
uspto-grants-1994_10
Patent number
US05354730

Reaction notes

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