Toluene → HCID 86668164, compound

HRID 385065Notes

Reaction equation

HRID 385065 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:14]#[CH:15])[C:11]=1[O:12][CH3:13])[C:6](O)=[O:7])#[N:2].C1(C)C=CC=CC=1.C(Cl)(=O)C([Cl:26])=O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:14]#[CH:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:26])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 86668163HCID 86668163, compound

Product 1

HCID 86668164HCID 86668164, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-cyano-5-ethynyl-4-methoxybenzoic acid (610 mg), toluene (6 mL), N,N-dimethylformamide (1 droplet) and oxalyl chloride (0.32 mL) were added to the solution under ice cooling, and the mixture was stirred at room temperature for 1.5 hours. The solvent was distilled off under reduced pressure and the obtained residue was azeotroped with toluene and used for the synthesis of (c).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe obtained residue was azeotroped with toluene
  3. customused for the synthesis of (c)

Sources & evidence

ORD record
ord-35956463f9a041828e0ccf039d357097
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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