4-(Trifluoromethyl)aniline → HCID 86707269, compound

HRID 576051Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[Cl:12][C:13]([Cl:30])([Cl:29])[C:14]([N:16]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=2)[CH2:17]1)=[O:15]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:30][C:13]([Cl:12])([Cl:29])[C:14]([N:16]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([S:25]([NH:7][C:6]3[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=3)(=[O:27])=[O:26])[CH:22]=2)[CH2:17]1)=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-trifluoromethyl aniline (213 μL, 1.70 mmol) in pyridine (270 μL) was added 2-(trichloroacetyl)-2,3-dihydro-1 H-isoindole-5-sulfonyl chloride (617 mg, 1.70 mmol) at room temperature, and the mixture was stirred at 60° C. for 1.5 hr. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate. The mixture was washed with 1 mol/L hydrochloric acid, brine and water. The organic layer was dried over anhydrous sodium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1) to afford the title compound as a colorless powder (586 mg).

Workup

temperatureto cool to room temperature
washThe mixture was washed with 1 mol/L hydrochloric acid, brine and water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationthe desiccant was filtered off
concentrationfollowed by concentration under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record: ord-9c8a67ed87b74650aeb003c8cf2d7f1a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035059B2

Reaction notes

Loading…