Reaction SMILES: Br[CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:3]=O.BrC1(Br)C(=O)NC(=O)NC1=O.C1(C(C)C=O)C=CC=CC=1.[CH3:33][S:34](=[O:51])([CH:39]([C:41]1[CH:42]=[N:43][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:45][CH:46]=1)[CH3:40])=[N:35][C:36]([NH2:38])=[S:37]>C(OCC)C.CCO>[CH2:5]([C:2]1[S:37][C:36]([N:35]=[S:34]([CH:39]([C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:48])([F:49])[F:50])=[N:43][CH:42]=2)[CH3:40])([CH3:33])=[O:51])=[N:38][CH:3]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
Reactant: CC(c1ccc(C(F)(F)F)nc1)S(C)(=O)=NC(N)=S
Reactant: O=CC(Br)Cc1ccccc1
Agent: CC(C=O)c1ccccc1
Agent: O=C1NC(=O)C(Br)(Br)C(=O)N1
Solvent: CCOCC
Solvent: CCO
Product: CC(c1ccc(C(F)(F)F)nc1)S(C)(=O)=Nc1ncc(Cc2ccccc2)s1
Temperature: 25 °C
Reaction time: 120 h

Procedure:
Preparation of 2-bromo-3-phenylpropanal: dibromobarbituric acid (1.43 g, 5 mmol) was dissolved in diethylether (40 mL) and phenylpropionaldehyde (1.34 g, 1.33 mL, 10 mmol) was added. After stirring at room temperature for 5 days, precipitation of barbituric acid was observed. The reaction mixture was filtered and washed with sat. aq. NaHCO3 (1×40 mL), and brine (2×40 mL). The mixture was dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. GC-MS analysis of the concentrate showed 2-bromo-3-phenylpropanal as the sole product. (2) Preparation of (61): N-(methyl(oxo){1-[6-(trifluoromethyl)-3-pyridinyl]ethyl}-λ6-sulfanylidene)thiourea (J) (100 mg, 0.321 mmol) was suspended in EtOH (1 mL) and 2-bromo-3-phenylpropanal (82 mg, 0.385 mmol, 1.2 eq) in EtOH (0.6 mL) was added. The reaction was stirred at r.t. for 1 h, and then heated to reflux for 30 min. The solvent was removed under reduced pressure and the residue purified by preparative reverse-phase column chromatography (water/acetonitrile). 5-{1-[(5-benzyl-1,3-thiazol-2-yl)(methyl)sulfonimidoyl]ethyl}-2-(trifluoromethyl)pyridine (61) was obtained in form of a yellowish oil (26 mg, 0.061 mmol, 19%) as a racemate and 1:1 mixture of diastereomers. 1H-NMR (CDCl3, 400 MHz): δ=1.89 (d, J=7.2 Hz, 1.5H, CHCH3, diastereomer 1); 1.92 (d, J=7.2 Hz, 1.5H, CHCH3, diastereomer 2); 3.09 (s, 1.5H, S—CH3, diastereomer 1); 3.20 (s, 1.5H, S—CH3, diastereomer 2); 3.94 (s, 1H, CH2Ph, diasteromer 1), 3.97 (s, 1H, CH2Ph, diasteromer 2); 5.14 (q, J=7.2 Hz, 0.5H, CHCH3, diastereomer 1); 5.21 (q, J=7.2 Hz, 0.5H, CHCH3, diastereomer 2); 6.90 (s, 0.5H, thiazole, diastereomer 1); 6.92 (s, 0.5H, thiazole, diastereomer 2); 7.15-7.37 (m, 5H, Ph); 7.71 (d, J=8.2 Hz, 0.5H, pyr-C3-H, diastereomer 1), 7.72 (d, J=8.2 Hz, 0.5H, pyr-C3-H, diastereomer 2); 8.09 (dd, 3J=8.2 Hz, 4J=1.8 Hz, 0.5H, pyr-C4-H, diastereomer 1); 8.12 (dd, 3J=8.2 Hz, 4J=1.7 Hz, 0.5H, pyr-C4-H, diastereomer 2); 8.75 (d, 4J=1.8 Hz, 0.5H, pyr-C6-H, diastereomer 1); 8.79 (d, 4J=1.8 Hz, 0.5H, pyr-C6-H, diastereomer 2); 13C-NMR (CDCl3, 100 MHz): δ=13.8, 14.2 (CHCH3, two diastereomers); 33.2. 33.3 (CH2Ph, two diastereomers); 36.5, 36.8 (S—CH3, two diastereomers); 60.8, 61.6 (CHCH3, two diastereomers); 119.5, 119.6 (pyr-C, 2 diastereomers); 125.6, 125.7 (Ph, two diastereomers), 127.2, 127.3 (Ph, two diastereomers, 127.5 (Ph, two diastereomers), 130.1, 130.2 (pyr-C, two diastereomers), 131.1, 131.5, (pyr-C, two diastereomers), 132.7, 133.2 (thiazole, two diastereomers), 137.3, 137.6 (pyr-C, 2-diastereomers); 137.9, 138.0 (thiazole, two diastaereomers); 149.2, 149.4 (pyr-C, 2-diastereomers); 165.6, 165.8 (thiazole, two diastereomers); CF3, not detected. UPLC-MS (ESI+): mass calc'd for C19H19F3N3OS2 (M+H+): 426.1, found 426.1, UPLC-MS (EST) mass calc'd for C19H17F3N3OS2 (M−H+): 424.1, found 424.1.