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

HRID 583195Notes

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.CN(C)C=O.[H-].[Na+].[F:20][C:21]([F:38])([F:37])[C:22]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:31]=2)[CH2:26][CH2:25]1)=[O:23]>O>[C:1]1([C:7]2[NH:8][C:9](=[O:12])[N:10]([S:33]([C:29]3[CH:28]=[C:27]4[C:32](=[CH:31][CH:30]=3)[N:24]([C:22](=[O:23])[C:21]([F:38])([F:20])[F:37])[CH2:25][CH2:26]4)(=[O:34])=[O:35])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

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 m 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

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

Sources & evidence

ORD record: ord-89c8db0c95364519b2618e9660a3efd2
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05929103

Reaction notes

Loading…