Toluene → HCID 86668162, compound

HRID 385061Notes

Reaction equation

HRID 385061 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH:14]2[CH2:16][CH2:15]2)[C:11]=1[O:12][CH3:13])[C:6](O)=[O:7])#[N:2].C1(C)C=CC=CC=1.S(Cl)([Cl:26])=O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH:14]2[CH2:16][CH2:15]2)[C:11]=1[O:12][CH3:13])[C:6]([Cl:26])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 68108477HCID 68108477, compound

Product 1

HCID 86668162HCID 86668162, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-cyano-5-cyclopropyl-4-methoxybenzoic acid (200 mg), toluene (2 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.10 mL) were added, and the mixture was stirred at 60° C. for 16 hours. The solvent was distilled off under reduced pressure and the obtained resiue was azeotroped with toluene and used for the synthesis of (d).

Workup

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

Sources & evidence

ORD record
ord-61dc30bb2440491c8f1e6ec259b65249
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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