Toluene → 3-Cyano-5-cyclobutyl-4-methoxybenzoyl chloride

HRID 385052Notes

Reaction equation

HRID 385052 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH:14]2[CH2:17][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:27])=O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH:14]2[CH2:17][CH2:16][CH2:15]2)[C:11]=1[O:12][CH3:13])[C:6]([Cl:27])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 681083433-Cyano-5-cyclobutyl-4-methoxybenzoic acid

Product 1

HCID 866681593-Cyano-5-cyclobutyl-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-cyano-5-cyclobutyl-4-methoxybenzoic acid (190 mg), toluene (2.0 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.07 mL) were added, and the mixture was stirred at 60° C. for 3 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene to obtain the title compound (204 mg) as a brown oily substance.

Workup

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

Sources & evidence

ORD record
ord-89a0cc75039c443591e82e32fd512c83
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

Loading…