Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][CH2:6][CH2:5]2.[O-:19][C:20]#[N:21].[Na+]>C(O)(=O)C.O>[C:12]1([C:11]2[NH:21][C:20](=[O:19])[NH:1][C:2]3[C:10]=2[CH:9]=[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]2[CH:3]=3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
Reactant: Nc1cc2c(cc1C(=O)c1ccccc1)CCC2
Reactant: N#C[O-]
Agent: [Na+]
Solvent: O
Solvent: CC(=O)O
Product: O=c1[nH]c(-c2ccccc2)c2cc3cccc3cc2[nH]1
Temperature: 25 °C
Reaction time: 3 h
Yield: 78.5 %

Procedure:
To a solution of 5-amino-6-benzoylindane (160 mg, 0.68 mmol) in 6 mL of acetic acid and 0.6 mL of water was added sodium cyanate (53 mg, 0.81 mmol) and the solution was stirred at rt for 3 h. Water was then added to produce a suspension which was filtered and washed with water. The resulting solid was dried under vacuum to give the title compound (139 mg, 79%). 1H NMR (CDCl3): 13.25 (bs,1H), 7.80 (d, 2H), 7.70 (s,1H), 7.60 (m, 4H), 3.05 (t, 2H), 2.95 (t, 2H), 2.15 (p, 2H).
Reaction SMILES: [O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:27]=[CH:26][C:13]2[N:14]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1.[OH-].[Na+].CO>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:27]=[CH:26][C:13]2[N:14]([CH2:18][C:19]([OH:21])=[O:20])[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1
Reactant: Cc1nc2cc(-c3nc4ccccc4o3)ccc2n1CC(=O)OC(C)(C)C
Agent: [Na+]
Agent: [OH-]
Solvent: CO
Solvent: ClC(Cl)Cl
Product: Cc1nc2cc(-c3nc4ccccc4o3)ccc2n1CC(=O)O
Temperature: 25 °C
Reaction time: 2 h
Yield: 91 %

Procedure:
To a solution of 5-(benzoxazol-2-yl)-2-methyl-1-tert-butoxycarbonylmethylbenzimidazole (see Working Example 91-2) (100 mg, 0.275 mmol) in chloroform (3 mL) was added aqueous sodium hydroxide solution (1 M, 0.55 mL, 0.55 mmol). This two-layer solution was homogenized by the addition of methanol, and this was stirred at room temperature for 2 hours. After the reaction was complete, the solution was concentrated, aqueous acetic acid solution was added, and this was stirred at room temperature. The precipitated crystals were filtered, and after washing with water were dried to yield the title compound (76.9 mg, 91% yield) as light yellow crystals.