Dimethylformamide → N-(1-Ethyl-hexahydro-5-methyl-2,4,6-trioxo-5-pyrimidinyl)-2,3,4,5-tetrafluorobenzamide

HRID 1097279Notes

Reaction equation

HRID 1097279 reaction equation
[NH2:1][C:2]1([CH3:13])[C:7](=[O:8])[N:6]([CH2:9][CH3:10])[C:5](=[O:11])[NH:4][C:3]1=[O:12].[F:14][C:15]1[C:16]([F:28])=[C:17]([F:27])[C:18]([F:26])=[C:19]2C(=O)O[C:21](=[O:22])[C:20]=12.CN(C=O)C>O>[CH2:9]([N:6]1[C:7](=[O:8])[C:2]([NH:1][C:21](=[O:22])[C:20]2[CH:19]=[C:18]([F:26])[C:17]([F:27])=[C:16]([F:28])[C:15]=2[F:14])([CH3:13])[C:3](=[O:12])[NH:4][C:5]1=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 69545Tetrafluorophthalic anhydrideHCID 668110525-Amino-1-ethyl-5-methylbarbituric acid

Product 1

HCID 24765666N-(1-Ethyl-hexahydro-5-methyl-2,4,6-trioxo-5-pyrimidinyl)-2,3,4,5-tetrafluorobenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-amino-1-ethyl-5-methylbarbituric acid (0.37 g, 2 mmol), tetrafluorophthalic anhydride (0.44 g, 2 mmol) and DMF (14 mL) was stirred under reflux for 5 hours. The yellow solution was then allowed to cool down to room temperature and poured into water (50 mL). The precipitate that formed was collected by filtration and dried under reduced pressure to give 20f as white crystals.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe precipitate that formed
  3. filtrationwas collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-21bb8e162ac1474f9b0f9c250b125d97
Source dataset
uspto-grants-2012_03
Patent number
US08143252B2

Reaction notes

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