Triethylamine → HCID 23284729, compound

HRID 369322Notes

Reaction equation

HRID 369322 reaction equation
Br.[F:2][C:3]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:12])=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.C(O[CH:23]=[C:24]([C:30](=[O:43])[C:31]1[CH:36]=[C:35]([F:37])[C:34]([N+:38]([O-:40])=[O:39])=[C:33]([CH3:41])[C:32]=1F)[C:25]([O:27][CH2:28][CH3:29])=[O:26])C>C(Cl)(Cl)Cl>[F:2][C:3]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:12])=[CH:6][C:4]=1[N:5]1[C:32]2[C:31](=[CH:36][C:35]([F:37])=[C:34]([N+:38]([O-:40])=[O:39])[C:33]=2[CH3:41])[C:30](=[O:43])[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23284727HCID 23284727, compoundHCID 53814737Ethyl α-(ethoxymethylene)-2,5-difluoro-3-methyl-4-nitro-β-oxobenzenepropanoate

Product 1

HCID 23284729HCID 23284729, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2,4-Difluoro-5-methoxyaniline monohydrobromide (780 mg) and a solution of triethylamine (328 mg) in chloroform (10 ml) were added dropwise to a solution of ethyl 3-ethoxy-2-(2',5'-difluoro-3'-methyl-4'-nitrobenzoyl)acrylate (2.0 g) in chloroform (10 ml) at 0° C. After the mixture was stirred for 10 minutes, the solvent and the like were distilled off. Anhydrous potassium carbonate (510 mg) was added to a solution of the whole amount of the residue in N,N-dimethylformamide (10 ml), and the mixture was stirred at 70° C. for 5 hours. Ethyl acetate and water were added to the reaction mixture to collect an organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off. Ethanol was added to the residue to disperse it therein, and filtration was conducted to obtain the title compound (660 mg) as a pale yellow powder.

Workup

  1. distillationthe solvent and the like were distilled off
  2. additionAnhydrous potassium carbonate (510 mg) was added to a solution of the whole amount of the residue in N,N-dimethylformamide (10 ml)
  3. stirringthe mixture was stirred at 70° C. for 5 hours
  4. additionEthyl acetate and water were added to the reaction mixture
  5. customto collect an organic layer
  6. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. additionEthanol was added to the residue
  9. additionto disperse it
  10. filtrationfiltration

Sources & evidence

ORD record
ord-f1e254ad0b4a4389b5bdbfdc437a1add
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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