Thionyl Chloride → 1-Phenyl-1H-1,2,4-triazole-3-carbonyl chloride

HRID 334077Notes

Reaction equation

HRID 334077 reaction equation
[C:1]1([N:7]2[CH:11]=[N:10][C:9]([C:12]([OH:14])=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:17])=O>C(Cl)Cl.CN(C=O)C>[C:1]1([N:7]2[CH:11]=[N:10][C:9]([C:12]([Cl:17])=[O:14])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 123160561-Phenyl-1H-1,2,4-triazole-3-carboxylic acid

Product 1

HCID 866882991-Phenyl-1H-1,2,4-triazole-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 2.00 g (10.5 mmol) 1-phenyl-1H-[1,2,4]-triazole-3-carboxylic acid in 20 mL DCM was added 10.0 mL (137 mmol) thionyl chloride and 1 drop of DMF. The reaction mixture was stirred at 40° C. for 1 h. The solvent was removed by distillation. Yield: 2.20 g (100%); ESI-MS: m/z=204 (M+H)+ (methyl ester); Rt(HPLC): 1.04 min (method 8) (methyl ester)

Workup

  1. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-53902d0fa039462bb0469a0db92409f9
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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