Dimethylformamide → HCID 86709877, compound

HRID 2206982Notes

Reaction equation

HRID 2206982 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:17]([OH:19])=O)[CH:3]=1.S(Cl)([Cl:22])=O.CN(C)C=O.CN(C1C=CC=CN=1)C>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:17]([Cl:22])=[O:19])[CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 218852-DimethylaminopyridineHCID 24386Thionyl ChlorideHCID 86709870HCID 86709870, compound

Product 1

HCID 86709877HCID 86709877, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of 4,5-dichloro-6-(4-methoxyphenyl)-picolinic acid (4.50 g, 15.1 mmol) in toluene (40 mL) was added thionyl chloride (1.65 mL, 22.6 mmol) and dimethylformamide (0.06 mL, 0.8 mmol). Reaction mixture was heated at 80° C. for 12 h. HPLC analysis of an aliquot treated with methanol and dimethylaminopyridine indicated complete conversion of the starting material. Reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to provide a yellow solid. Toluene (40 mL) was added to dissolve the solid and concentrated under reduced pressure and then this process was performed a second time. 4,5-Dichloro-6-(4-methoxyphenyl)-picolinoyl chloride was isolated as a yellow solid (4.64 g, 97% yield). 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.85-7.77 (m, 2H), 7.06-6.98 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 168.91, 161.06, 158.35, 146.26, 145.13, 133.92, 131.35, 129.16, 124.13, 113.70., LRMS. Calcd. for C13H8Cl3NO2: 314.96. Found: m/z=253 (M+-COCl), 218.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperatureto cool to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customto provide a yellow solid
  6. dissolutionto dissolve the solid
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d058e68e2514a2f9e3241ca46dfdd65
Source dataset
uspto-grants-2016_06
Patent number
US09376388B2

Reaction notes

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