Chlorosulfonic acid → HCID 59596724, compound

HRID 1807554Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2)=[O:4].[Cl:18][S:19](O)(=[O:21])=[O:20]>CCOC(C)=O>[F:17][C:2]([F:1])([F:16])[C:3]([NH:5][C:6]1[C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]([S:19]([Cl:18])(=[O:21])=[O:20])=[CH:8][CH:7]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

Under N2 at 25° C., 2,2,2-trifluoro-N-(quinolin-8-yl)acetamide (5.0 g, 20.8 mmol) was added to chlorosulfonic acid (15 ml) and then heated at 80° C. for 19 h. The mixture was then poured into ice-water (200 ml), followed by addition of EtOAc (300 ml). The organic layer was passed through a short bed of silica gel followed by EtOAc (700 ml) and then evaporated and triturated with Et2O to give the product as a light tan solid (2.2 g, 31%). 1H NMR (400 MHz, CDCl3) δ 11.02 (s, 1H), 9.19 (dd, J=8.8, 1.4 Hz, 1H), 9.05 (dd, J=4.2, 1.4 Hz, 1H), 8.84 (d, J=8.5 Hz, 1H), 8.48 (d, J=8.5 Hz, 1H), 7.85 (dd, J=8.8, 4.2 Hz, 1H).

Workup

customevaporated
customtriturated with Et2O

Sources & evidence

ORD record: ord-30906e95e91c42498af7f1c69c78bdf9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357702B2

Reaction notes

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