Reaction equation
[CH3:1][S:2][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[N:9][CH:10]=1)[CH3:4].[N:18]#[C:19][NH2:20].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C1COCC1>[F:16][C:11]([F:17])([C:8]1[N:9]=[CH:10][C:5]([CH:3]([S:2]([CH3:1])=[N:20][C:19]#[N:18])[CH3:4])=[CH:6][CH:7]=1)[C:12]([F:13])([F:14])[F:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of the 5-(1-methylthioethyl)-2-pentafluoro-ethylpyridine (A) (0.16 g, 0.6 mmol) and cyanamide (0.025 g, 0.6 mmol) in THF (3 mL) cooled to 0° C. was added iodobenzene diacetate (0.19 g, 0.6 mmol) in one portion and the resulting mixture was stirred at 0° C. for 2 h and then at room temperature overnight. The solvent was removed in vacuo and the resulting mixture was suspended in brine-saturated NaHCO3 (9:1), which was then extracted with CH2Cl2-EtOAc (1:1, v/v) two times. The combined organic layer was dried over Na2SO4, filtered, concentrated, and dried to give 0.16 g of (1-{6-[pentafluoroethyl]pyridin-3-yl}ethyl)(methyl)-λ4-sulfanylidenecyanamide (B) as a brownish oil in 85 percent yield. LC-MS: mass calcd for C11H10F5N3S [M]+ 311.28. Found [M−1]+ 309.84.
Workup
- customat room temperature
- customovernight
- customThe solvent was removed in vacuo
- extractionwhich was then extracted with CH2Cl2-EtOAc (1:1
- dry with materialThe combined organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customdried
Sources & evidence
- ORD record
- ord-0aaefce838364358a21f1fbeea2d9c77
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846717B2
Linked notes
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