Water → 1,3-Bis(2-chlorothiophenoyl)Benzene

HRID 37332

Reaction equation

HRID 37332 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7](Cl)(=[O:17])[C:8]1[CH:16]=[CH:15][CH:14]=[C:10]([C:11](Cl)=[O:12])[CH:9]=1.[Cl-:19].[Al+3].[Cl-].[Cl-].O>C(=S)=S>[Cl:1][C:2]1([C:7]([C:8]2[CH:16]=[CH:15][CH:14]=[C:10]([C:11]([C:4]3([Cl:19])[CH2:5][CH:6]=[CH:2][S:3]3)=[O:12])[CH:9]=2)=[O:17])[CH2:6][CH:5]=[CH:4][S:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 72992-ChlorothiopheneHCID 7451Isophthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 677840041,3-Bis(2-chlorothiophenoyl)BenzeneYield 75%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

A solution of 2-chlorothiophene (0.128 mol) in 20 mL of carbon disulfide was added to a stirred suspension of isophthaloyl chloride (0.064 mol) and anhydrous aluminum chloride (0.1408 mol) in 100 mL of carbon disulfide. The reaction mixture was heated to reflux, stirred under nitrogen for 3 hours, and poured into 300 mL of water. The organic layer was separated immediately, then washed twice with 3.00 mL of 10% NaOH, twice with 300 mL of 5% HCl, and once with 500 mL of water. The product was recrystallized twice from ethyl acetate to form light yellow crystals in a 75% yield. Purity was determined by GC to be greater than 99.9%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customThe organic layer was separated immediately
  4. washwashed twice with 3.00 mL of 10% NaOH, twice with 300 mL of 5% HCl
  5. customThe product was recrystallized twice from ethyl acetate
  6. customto form light yellow crystals in a 75% yield

Sources & evidence

ORD record
ord-9e5555306d5d4ec291cd6d21577f16ab
Source dataset
uspto-grants-1995_05
Patent number
US05420224

Linked notes

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