Potassium Carbonate → HCID 54169532, compound

HRID 849444Notes

Reaction equation

HRID 849444 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([C:16]([Cl:37])=[CH:17][C:18]1[CH:19]=[C:20]([N:24]2[C:29](=[O:30])[CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]([CH3:35])[C:25]2=[O:36])[CH:21]=[CH:22][CH:23]=1)([OH:15])=O.[ClH:38].[CH3:39][O:40][NH2:41].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:38][C:23]1[CH:22]=[CH:21][C:20]([N:24]2[C:29](=[O:30])[CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[N:26]([CH3:35])[C:25]2=[O:36])=[CH:19][C:18]=1[CH:17]=[C:16]([Cl:37])[C:13]([NH:41][O:40][CH3:39])=[O:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 54479117HCID 54479117, compound

Product 1

HCID 54169532HCID 54169532, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Carbonyldiimidazole (0.9 g) was added to a solution of 3-[3-(2-carboxy-2-chloroethenyl)phenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine (2.1 g) in 80 ml of tetrahydrofuran, after which the mixture was stirred at 25° C. for one hour. Methoxyamine hydrochloride (1.67 g as a 30% strength by weight aqueous solution) and potassium carbonate (0.83 g), dissolved in 20 ml of tetrahydrofuran, were then added dropwise. After stirring for 5 hours, the solvent was distilled off, after which the residue was taken up in 150 ml of dichloromethane. The organic phase was washed twice with 30 ml each of water, twice with 30 ml each of 10% strength by weight sodium hydrogencarbonate solution and again with 30 ml of water, then dried over sodium sulfate and concentrated. After crystallization using petroleum ether, 1.5 g of the product were obtained; m.p.: 136-141° C.

Workup

  1. additionwere then added dropwise
  2. stirringAfter stirring for 5 hours
  3. distillationthe solvent was distilled off
  4. washThe organic phase was washed twice with 30 ml each of water, twice with 30 ml each of 10% strength by weight sodium hydrogencarbonate solution and again with 30 ml of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customAfter crystallization

Sources & evidence

ORD record
ord-711e4ddf254b47329f760189360d3cb2
Source dataset
uspto-grants-2000_01
Patent number
US06013606

Reaction notes

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