Triethylamine → 3-Chloro-1-((4-fluorophenyl)amino)-4-phenylpyrrol-2,5-dione

HRID 1355334Notes

Reaction equation

HRID 1355334 reaction equation
[Cl:1][C:2]1[C:3](=[O:14])O[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:3](=[O:14])[N:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 234471953-Chloro-4-phenylfuran-2,5-dione

Product 1

HCID 234471963-Chloro-1-((4-fluorophenyl)amino)-4-phenylpyrrol-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.13 g (15 mmol) of 3-chloro-4-phenylfuran-2,5-dione and 2.44 g (15 mmol) of 4-fluorophenylhydrazine hydrochloride were initially charged in 50 ml of methylene chloride, and the mixture was, at room temperature, admixed dropwise with stirring with 1.52 g (15 mmol) of triethylamine and stirred at room temperature overnight. A further 50 ml of methylene chloride were added, and the mixture was washed three times with in each case 80 ml of water, dried over sodium sulfate and concentrated under reduced pressure. Yield: 3.9 g of a crystalline solid, m.p. 115-117° C.

Workup

  1. customwas, at room temperature
  2. washthe mixture was washed three times with in each case 80 ml of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ae6ee306fb642b483dc236143e3c418
Source dataset
uspto-grants-2003_07
Patent number
US06586369B1

Reaction notes

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