Water → HCID 19023221, compound

HRID 1034137Notes

Reaction equation

HRID 1034137 reaction equation
[F:1][C:2]1[C:15]([NH:16][C:17](OC)=[O:18])=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[NH2:21]/[C:22](/[C:29]([F:32])([F:31])[F:30])=[CH:23]\[C:24]([O:26]CC)=O.[H-].[Na+].O>CN(C)C=O>[F:1][C:2]1[C:15]([N:16]2[C:24](=[O:26])[CH:23]=[C:22]([C:29]([F:30])([F:31])[F:32])[NH:21][C:17]2=[O:18])=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 19023224HCID 19023224, compound

Product 1

HCID 19023221HCID 19023221, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-fluoro-6-methoxycarbonylamino-4-propargyl-2H-1,4-benzoxazin-3(4H)-one (1.4 g) and ethyl 3-amino-4,4,4-trifluorocrotonate was dissolved in dimethylformamide (5 g), and sodium hydride (0.2 g) was added thereto. The resultant mixture was stirred for 30 minutes while cooling with ice and 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-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione (0.2 g).

Workup

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

Sources & evidence

ORD record
ord-7924f7eede9746678962a94cf7a85fdb
Source dataset
uspto-grants-1994_05
Patent number
US05314864

Reaction notes

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