Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]([O:3][C:4](=[O:17])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:2].[CH2:18]=O.[CH:20]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([F:34])([F:33])[F:32])(=[O:24])=[O:23])=[CH2:21]>>[CH2:1]([O:3][C:4]([CH:5]1[CH2:18][CH:20]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:32])([F:34])[F:33])(=[O:23])=[O:24])[CH2:21][N:6]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:17])[CH3:2]
Reactant: CCOC(=O)CNc1ccccc1C(C)(C)C
Reactant: C=O
Reactant: C=CS(=O)(=O)c1ccccc1C(F)(F)F
Product: CCOC(=O)C1CC(S(=O)(=O)c2ccccc2C(F)(F)F)CN1c1ccccc1C(C)(C)C

Procedure:
In analogy to the procedure described in example 343d, (2-tert-butyl-phenylamino)-acetic acid ethyl ester (CAS Reg. No. 959563-17-8) was reacted with paraformaldehyde and 1-ethenesulfonyl-2-trifluoromethyl-benzene (example 243c) to give the title compound as colorless oil. MS (ESI): m/z=484.4 [M+H]+.
Reaction SMILES: [H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]([CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[N:7]=[C:6]([NH:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[N:5]=1.C[O:29][C:30](=[O:33])[CH2:31]Cl.[CH3:34]N(C=O)C>>[CH3:34][CH:31]([C:30]([OH:29])=[O:33])[N:19]([C:20]1[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=1)[C:6]1[N:5]=[C:4]([NH2:3])[N:9]=[C:8]([CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[N:7]=1
Reactant: CN(C)C=O
Reactant: COC(=O)CCl
Reactant: N#Cc1ccc(Nc2nc(N)nc(Cc3c(Cl)cccc3Cl)n2)cc1
Agent: [H-]
Agent: [Na+]
Product: CC(C(=O)O)N(c1ccc(C#N)cc1)c1nc(N)nc(Cc2c(Cl)cccc2Cl)n1
Temperature: 70 °C
Reaction time: 0.08 h
Yield: 19.4 %

Procedure:
A solution of sodium hydride (0.00195 mol) in DMF (7 ml) was added to compound (1) (0.00186 mol) and the resulting solution was stirred for 5 minutes under argon. Then, chloroacetic acid methyl ester (0.0186 mol) was added and the reaction mixture was heated to 70° C. for 19 hours. The reaction mixture was then quenched with water and the resulting solid was filtered off. The residue was treated with hot ACN, then filtered while still hot. The residue from the cooled filtrate was recrystallized from 1,4-dioxane. The precipitate was filtered off, yielding 0.16 g (19.4%) of methyl N-(4-cyanophenyl)-N-[4-amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]glycine (compound 39).