Water → 4-phenyl-1-(N-trifluoroacetylindoline-5-sulfonyl)-2-imidazolone

HRID 1584656Notes

Reaction equation

HRID 1584656 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:12])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:15][C:16]([F:33])([F:32])[C:17]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([S:28](Cl)(=[O:30])=[O:29])=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)=[O:18].O>CN(C)C=O>[C:1]1([C:7]2[NH:8][C:9](=[O:12])[N:10]([S:28]([C:24]3[CH:23]=[C:22]4[C:27](=[CH:26][CH:25]=3)[N:19]([C:17](=[O:18])[C:16]([F:33])([F:15])[F:32])[CH2:20][CH2:21]4)(=[O:29])=[O:30])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 110626774-phenyl-2,3-dihydro-1H-imidazol-2-oneHCID 110883061-(Trifluoroacetyl)-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 212248744-phenyl-1-(N-trifluoroacetylindoline-5-sulfonyl)-2-imidazoloneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Phenyl-2,3-dihydro-1H-2-imidazolone (4 g, 24.84 mmol) prepared in Preparation 1 was suspended in 30 ml of dimethylformamide and cooled down to 0 ° C. After sodium hydride (60% oily, 1.09 g, 27.3 mmol) was added thereto, the resulting mixture was stirred for a few minutes at 0° C. until it became a clear solution. To the reaction mixture was added portionwise at 0° C. the N-trifluoroacetyl-indoline-5-sulfonylchloride (8.56 g, 27.32 mmol) prepared in Preparation 2. The reaction mixture was stirred at room temperature for 4 hours, cooled down again to 0° C., and then water was slowly added to the mixture until precipitate was formed. The resulting precipitate was collected, washed with water, and dried to afford 7.6 g of 4-phenyl-1-(N-trifluoroacetylindoline-5-sulfonyl)-2-imidazolone.

Workup

  1. customprepared in Preparation 2
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. temperaturecooled down again to 0° C.
  4. customwas formed
  5. customThe resulting precipitate was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-4fb762a2e3904d59ab7ae167953b0f9c
Source dataset
uspto-grants-1999_08
Patent number
US05932742

Reaction notes

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