Dimethylformamide → HCID 58468226, compound

HRID 571652Notes

Reaction equation

HRID 571652 reaction equation
[N:1]1[N:2]([C:6]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:7]=2[C:8](O)=[O:9])[N:3]=[CH:4][CH:5]=1.C(Cl)(=O)C([Cl:19])=O.CN(C=O)C>C(Cl)Cl>[CH3:15][C:12]1[CH:13]=[CH:14][C:6]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[C:7]([CH:11]=1)[C:8]([Cl:19])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Product 1

HCID 58468226HCID 58468226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid (15, 3.56 g, 17.52 mmol) in DCM (150 mL) cooled to 0° C. was added oxalyl chloride (1.90 mL, 21.9 mmol) and DMF (68 μL, 0.89 mmol). The solution was slowly warmed to ambient temperature and stirred overnight. The mixture was concentrated in vacuo and the resulting solid was azeotroped with DCM and concentrated in vacuo to provide 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl chloride (3) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting solid was azeotroped with DCM
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6332a77d9dfc4e1fadb1e550151879e3
Source dataset
uspto-grants-2015_05
Patent number
US09029364B2

Reaction notes

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