Ethanethiol → HCID 67133599, compound

HRID 222550Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[CH2:7]([SH:9])[CH3:8].Cl[C:11]1[C:20]([NH:21][C:22](=[O:29])[CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][C:18]2[C:13](=[CH:14][C:15]([C:30]([F:33])([F:32])[F:31])=[CH:16][CH:17]=2)[N:12]=1.CCCCCC.CC(=O)OCC>CN(C=O)C.O>[CH2:7]([S:9][C:11]1[C:20]([NH:21][C:22](=[O:29])[CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[CH:19][C:18]2[C:13](=[CH:14][C:15]([C:30]([F:31])([F:32])[F:33])=[CH:16][CH:17]=2)[N:12]=1)[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

331 mg (2.4 mmol) of K2CO3 and 40 mg (1.6 mmol) of ethanethiol were added to a solution of 300 mg (0.81 mmol) of N-(2-chloro-7-(trifluoromethyl)quinolin-3-yl)-2-(thiophen-2-yl)acetamide in DMF (6 ml), and the mixture was heated for 16 h at 60° C. It was then diluted with water and extracted with EA. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 9:1) of the residue yielded 242 mg (0.6 mmol, 74%) of N-[2-ethylsulfanyl-7-(trifluoromethyl)-quinolin-3-yl]-2-thiophen-2-yl-acetamide. MS: m/z 397.1 [M+H]+.

Workup

extractionextracted with EA
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4d87163048f24763bbc005f6e975653a
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207342B2

Reaction notes

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