Thiophene → HCID 12525776, compound

HRID 2308586Notes

Reaction equation

HRID 2308586 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[S:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([C:12]1[S:11][CH:15]=[CH:14][CH:13]=1)=[O:5]

Participants

5

Reactant 3

HCID 8030ThiopheneHCID 691102-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12525776HCID 12525776, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a cooled solution of 58 mL of o-chlorobenzoyl chloride and 24 mL of thiophene in 700 mL of carbon disulfide, cooled to 0° C. under a nitrogen atmosphere, was added 134 g of aluminum trichloride portionwise over a 20-minute period. A delayed exotherm was noted and the resulting deep red mixture was stirred for one hour at room temperature. Reaction mixture was poured into 4.0 kg of ice-water, extracted with methylene chloride and the organic layer washed three times with 1N NaOH followed by a final water wash. The organic layer was dried (MgSO4), filtered and concentrated to a dark oil. Distillation under vacuum provided 55 g of the subject compound as a light green viscous liquid, B.P. 160° C. at 1.6 mm.

Workup

  1. customReaction mixture
  2. extractionextracted with methylene chloride
  3. washthe organic layer washed three times with 1N NaOH
  4. washwash
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a dark oil
  8. distillationDistillation under vacuum

Sources & evidence

ORD record
ord-cfd3348114664328a1936380bc0283ae
Source dataset
uspto-grants-1987_09
Patent number
US04690705

Reaction notes

Loading…