Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:19](Cl)(=[O:21])=[O:20])=[C:10]2[O:15]C(=O)C)(=[O:3])[CH3:2].C(Cl)(Cl)Cl.C(=O)([O-])[O-].[NH4+:31].[NH4+].Cl>O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:19]([NH2:31])(=[O:21])=[O:20])=[C:10]2[OH:15])(=[O:3])[CH3:2]
Reactant: [NH4+]
Reactant: CC(=O)Nc1cccc2c(OC(C)=O)c(S(=O)(=O)Cl)ccc12
Agent: Cl
Agent: O=C([O-])[O-]
Solvent: ClC(Cl)Cl
Solvent: O
Product: CC(=O)Nc1cccc2c(O)c(S(N)(=O)=O)ccc12

Procedure:
The 5-acetamido-1-hydroxynaphthalene-2-sulfonamide was prepared by dissolving 10.8 g. of 5-acetamido-1-acetoxynaphthalene-2-sulfonyl chloride in 10 ml. dry chloroform and heating on the steam bath with 25.0 g. anhydrous ammonium carbonate for 2.5 hours. The yellow-brown solid was dissolved by heating with 50 ml. water on the steam bath for 4 hours. Acidification with dilute hydrochloric acid to pH 5 caused the sulfonamide to precipitate. It was filtered off, washed and dried, yielding 5.61 g. (63%).
Reaction SMILES: [Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19](O)=[O:20]>>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:19](=[O:20])[CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])=[CH:7][CH:6]=1
Reactant: ClCCOc1ccccc1
Reactant: O=C(O)Cc1ccccc1Cl
Product: O=C(Cc1ccccc1Cl)c1ccc(OCCCl)cc1

Procedure:
1-[4-(2-Chloroethoxy)phenyl]-2-(2-chlorophenyl)ethanoe is prepared according to the method described in the example 4a using 2-chloroethoxybenzene and 2-chlorophenylacetic acid as starting materials.