Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:9]([CH2:12][CH3:13])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.S(=O)(O)[O-].[Na+].[C-:32]#[N:33].[K+]>O>[CH2:14]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH2:12][CH3:13])[C@H:10]([OH:11])[C:32]#[N:33])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
Reactant: [C-]#N
Reactant: CC[C@@H](C=O)N(Cc1ccccc1)Cc1ccccc1
Agent: O=S([O-])O
Agent: [K+]
Agent: [Na+]
Solvent: C1COCCO1
Solvent: O
Product: CC[C@@H]([C@H](O)C#N)N(Cc1ccccc1)Cc1ccccc1
Temperature: 0 °C
Reaction time: 0.17 h

Procedure:
Under an atmosphere of argon, (S)-2-(dibenzylamino)butanal (8.55 g, 32.0 mmol, Eq: 1.00) was combined with dioxane (70 ml) to give a light yellow solution. The reaction was stirred for 10 min at 0° C. Then sodium bisulfite in water (40%, 26.5 ml) was added. The reaction was stirred for another 10 min at 0° C. Then potassium cyanide (8.33 g, 128 mmol, Eq: 4), diluted in water (35 ml) was added. The reaction was stirred overnight at RT. The reaction mixture was poured into water (75 ml) and extracted with ethyl acetate (2×75 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 40% ethyl acetate in heptane). The title compound was obtained as a light yellow oil (6.49 g, 68.9%, MS (m/e)=295.3 [M+H+]).
Reaction SMILES: [CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][S:10][CH3:11])[CH:6]=[CH:5][C:4]=1[C:12]1[NH:13][C:14]2[C:15]([N:20]=1)=[N:16][CH:17]=[CH:18][CH:19]=2.[OH:21]O.N>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][S:10]([CH3:11])=[O:21])[CH:6]=[CH:5][C:4]=1[C:12]1[NH:13][C:14]2[C:15]([N:20]=1)=[N:16][CH:17]=[CH:18][CH:19]=2
Reactant: OO
Reactant: COc1cc(CSC)ccc1-c1nc2ncccc2[nH]1
Agent: N
Solvent: O
Solvent: CC(=O)O
Product: COc1cc(CS(C)=O)ccc1-c1nc2ncccc2[nH]1
Temperature: 25 °C
Reaction time: 2 h

Procedure:
A quantity of 1.4 gm (4.9 mmol) of 2-(2'-methoxy-4'-methylthiomethyl-phenyl)-imidazo[4,5-b]pyridine was dissolved in 30 ml of glacial acetic acid and mixed with 3 ml of 30% hydrogen peroxide. After stirring for two hours at ambient temperature, the solution was diluted with 200 ml of water, made alkaline with concentrated ammonia solution, saturated with sodium chloride, and extracted three times with 30 ml of methylene chloride. The organic extracts were concentrated by evaporation, and the solid residue was purified by column chromatography (200 gm of silica gel; eluant: methylene chloride with 2 to 10% of ethanol).