Dichlorodimethylsilane → 3,4,5-Trimethoxybenzenethiol

HRID 583936Notes

Reaction equation

HRID 583936 reaction equation
Cl[Si](Cl)(C)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([S:18](Cl)(=O)=O)[CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15].CN1CCN(C)C1=O>ClCCCl.[Zn]>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([SH:18])[CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15]

Participants

6

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 151961583,4,5-Trimethoxybenzene-1-sulfonyl chloride

Product 1

HCID 151982403,4,5-Trimethoxybenzenethiol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
75 °C

Procedure

A room temperature suspension of zinc powder (430 mg, 6.56 mmol) and dichlorodimethylsilane (0.80 mL, 6.59 mmol) in 1,2-dichloroethane (15 mL) was treated with a solution of 3,4,5-trimethoxybenzenesulfonyl chloride (500 mg, 1.87 mmol) and 1,3-dimethyl-2-imidazolidinone (647 mg, 5.67 mmol) in 1,2-dichloroethane (15 mL). The reaction was heated to 75° C. for 1 hour, cooled to room temperature, filtered, and concentrated. The concentrate was dissolved in methanol, concentrated, dissolved in methanol, and concentrated. The concentrate was purified by flash column chromatography on silica gel with dichloromethane to provide the desired product.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe concentrate was dissolved in methanol
  5. concentrationconcentrated
  6. dissolutiondissolved in methanol
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-445946e6d5c14f6ba8f66604ddb30ac9
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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