Dimethylformamide → 7-methyl-9-oxo-thioxanthene-3-carbonyl Chloride

HRID 1985587Notes

Reaction equation

HRID 1985587 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]2[C:5]([S:6][C:7]3[CH:8]=[C:9]([C:17]([OH:19])=O)[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O.CN(C)C=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:15]=[C:14]2[C:5]([S:6][C:7]3[CH:8]=[C:9]([C:17]([Cl:22])=[O:19])[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 108259057-Methyl-9-oxothioxanthene-3-carboxylic acid

Product 1

HCID 108509407-methyl-9-oxo-thioxanthene-3-carbonyl ChlorideYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 7-methyl-9-oxothioxanthene-3-carboxylic acid (MTA), 50.0 g (0.185 mol), was dissolved in 350 ml of toluene and 415 ml (5.69 mol) of thionyl chloride using an overhead stirrer in a 2 liter 3-neck round bottom flask. N,N-Dimethylformamide (DMF), 2 ml, was added and the reaction was brought to reflux for 2 hours. After this time, the mixture was stirred at room temperature for 16 hours. The solvent was removed under vacuum and the product was azeotroped with 3×350 ml of toluene to remove the excess thionyl chloride. The product was recrystallized from 800 ml of chloroform and the resulting solid was placed in a vacuum oven for 16 hours at 45° C. to complete removal of solvent. The isolated product weighed 45.31 g (85% yield) and nuclear magnetic resonance spectroscopy (NMR) confirmed the desired structure. This product was used for the preparation of a photoreactive monomer as described in Example 2.

Workup

  1. temperatureto reflux for 2 hours
  2. customThe solvent was removed under vacuum
  3. customthe product was azeotroped with 3×350 ml of toluene
  4. customto remove the excess thionyl chloride
  5. customThe product was recrystallized from 800 ml of chloroform
  6. waitthe resulting solid was placed in a vacuum oven for 16 hours at 45° C.
  7. customremoval of solvent
  8. customThis product was used for the preparation of a photoreactive monomer

Sources & evidence

ORD record
ord-1cf45ad8de2f4df3849961a21e55924a
Source dataset
uspto-grants-2009_06
Patent number
US07547445B2

Reaction notes

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