Dimethylformamide → HCID 19780828, compound

HRID 2081144Notes

Reaction equation

HRID 2081144 reaction equation
[H-].[Na+].CN(C)C=O.[Cl:8][C:9]1[CH:25]=[CH:24][C:23]([N:26]2[C:31](=[O:32])[CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[NH:28][C:27]2=[O:37])=[CH:22][C:10]=1[C:11]([O:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12].[CH2:38](Br)[CH:39]=[CH2:40]>O>[Cl:8][C:9]1[CH:25]=[CH:24][C:23]([N:26]2[C:31](=[O:32])[CH:30]=[C:29]([C:33]([F:35])([F:34])[F:36])[N:28]([CH2:40][CH:39]=[CH2:38])[C:27]2=[O:37])=[CH:22][C:10]=1[C:11]([O:13][C:14]([CH3:20])([CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 19780818HCID 19780818, compound

Product 1

HCID 19780828HCID 19780828, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.35 g of sodium hydride (50% dispersion in white oil) is added to 40 ml of dimethylformamide while stirring. 2.9 g of ethyl 2-{2-chloro-5-[3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-benzoyloxy}-2-methyl-propionate [sic] are added portionwise as the solid. After completion of the addition the mixture is stirred at room temperature for a further hour. 1.2 g of allyl bromide are now added in one portion. The reaction mixture is stirred at room temperature for 18 hours and thereafter introduced into 100 ml of water at 0° C. The mixture is extracted twice with 150 ml of ethyl acetate each time. The organic phases are washed once with 100 ml of saturated sodium chloride solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel with ethyl acetate/n-hexane (1:4). There is obtained ethyl 2-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-(2-propenyl)-4 -trifluoromethyl-1(2H)-pyrimidinyl]-benzoyloxy}-2-methyl-propionate as an oil;

Workup

  1. additionAfter completion of the addition the mixture
  2. stirringis stirred at room temperature for a further hour
  3. stirringThe reaction mixture is stirred at room temperature for 18 hours
  4. extractionThe mixture is extracted twice with 150 ml of ethyl acetate each time
  5. washThe organic phases are washed once with 100 ml of saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography over silica gel with ethyl acetate/n-hexane (1:4)

Sources & evidence

ORD record
ord-8a3af44c642b4a4298e33f71417b24fc
Source dataset
uspto-grants-1993_02
Patent number
US05183492

Reaction notes

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