Toluene → HCID 86668168, compound

HRID 385079Notes

Reaction equation

HRID 385079 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].C1(C)C=CC=CC=1.S(Cl)([Cl:26])=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[C:10]=1[O:11][CH3:12])[C:5]([Cl:26])=[O:6]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 67041821HCID 67041821, compound

Product 1

HCID 86668168HCID 86668168, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-chloro-4-methoxy-5-trifluoromethylbenzoic acid (300 mg), toluene (3 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (0.13 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 residue was azeotroped with toluene and used for the synthesis of (e).

Workup

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

Sources & evidence

ORD record
ord-dd0132036f6c4bcb87bf1f9815fbcc19
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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