Dichlorodimethylsilane → 3,4,5-Trimethoxybenzenethiol

HRID 1059847Notes

Reaction equation

HRID 1059847 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-b2f46cdb7e7d4eef9c1707263fd4336a
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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