Thioguaiacol → HCID 11088283, compound

HRID 1815504Notes

Reaction equation

HRID 1815504 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[SH:27].C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([S:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][CH3:19])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 23642ThioguaiacolHCID 81531DiisopropylethylamineHCID 110563872,3-dichloro-4-formylphenyl trifluoromethanesulfonate

Product 1

HCID 11088283HCID 11088283, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2,3-Dichloro-4-trifluoromethanesufonyloxy-benzaldehyde (2.50 g) was dissolved in 6 mL acetonitrile. 2-Methoxybenzenethiol (2.55 g of 70% pure material, 50% excess) was added. With cooling 2.50 g diisopropylethylamine was added slowly. The solution was removed from the ice bath, whereon a solid formed. The solution was warmed in a 50 C waterbath for 5 minutes. More acetonitrile (5 mL) was added and the mixture was cooled in ice, and then filtered to get 2.047 g of product, m.p. 137-139C.

Workup

  1. additionwas added slowly
  2. customThe solution was removed from the ice bath, whereon a solid
  3. customformed
  4. temperatureThe solution was warmed in a 50 C waterbath for 5 minutes
  5. temperaturethe mixture was cooled in ice
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2f81845f231749eeb6fd125f498a27ab
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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