Toluene → HCID 86668171, compound

HRID 385103Notes

Reaction equation

HRID 385103 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([S:16]([CH3:19])(=[O:18])=[O:17])[C:13]=1[O:14][CH3:15])[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.S(Cl)([Cl:29])=O>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([S:16]([CH3:19])(=[O:18])=[O:17])[C:13]=1[O:14][CH3:15])[C:8]([Cl:29])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 68108641HCID 68108641, compound

Product 1

HCID 86668171HCID 86668171, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3-t-butyl-4-methoxy-5-methylsulfonyl benzoic acid (200 mg), toluene (4 mL), N,N-dimethylformamide (1 droplet) and thionyl chloride (80 μL) were added to the solution, and then 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 (f).

Workup

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

Sources & evidence

ORD record
ord-fb017e0608244839961e397750ff4574
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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