Toluene → HCID 86668167, compound

HRID 385073Notes

Reaction equation

HRID 385073 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([I:14])[C:11]=1[O:12][CH3:13])[C:6](O)=[O:7])#[N:2].C1(C)C=CC=CC=1.S(Cl)([Cl:24])=O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([I:14])[C:11]=1[O:12][CH3:13])[C:6]([Cl:24])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 68108929HCID 68108929, compound

Product 1

HCID 86668167HCID 86668167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-cyano-5-iodo-4-methoxybenzoic acid (512 mg), toluene (5 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.15 mL) were added, and the mixture was stirred at 60° C. for 15 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene to obtain the title compound (527 mg) as a pale yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-fcb9807f444c4c81818b5a6087d0ace5
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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