Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [C:1]([O:13]C)(=O)[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.O.[NH2:40][NH2:41]>C1COCC1.O>[C:6]1([C:4]2[NH:3][CH2:2][C:1](=[O:13])[NH:41][N:40]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
Reactant: NN
Reactant: COC(=O)CNC(=O)c1ccccc1
Agent: c1ccc(P(c2ccccc2)c2ccccc2)cc1
Solvent: C1CCOC1
Solvent: O
Solvent: ClC(Cl)(Cl)Cl
Product: O=C1CNC(c2ccccc2)=NN1
Temperature: 50 °C

Procedure:
To 5.8 g. of methyl hippurate dissolved in 35 ml THF was added 3.9 g. of triphenylphosphine and 10.0 g. of carbon tetrachloride in 15 ml THF. The mixture was heated to about 50° C. for 6 hours and 3.0 g. of hydrazine hydrate was added. The mixture was refluxed for about 18 hours, cooled and poured into water. The solution was extracted with ethyl acetate, and the organic phase was then extracted with 1 N HCl. The acidic extract was neutralized with 6 N sodium hydroxide and the product was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated under vacuum. The solid was recrystallized from methanol to yield about 0.200 g. of solid. Yield 4%. M.P.=212°-216° C.