Water → HCID 14770221, compound

HRID 2073574Notes

Reaction equation

HRID 2073574 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=[O:9])C=1Cl.O.[CH3:16][C:17]1[CH:33]=[CH:32][C:31]2[C:19](=[CH:20][C:21]3[S:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[C:22]=3[CH:30]=2)[CH:18]=1>C(Cl)(Cl)Cl>[CH:29]1[C:23]2[C:22]3[CH:30]=[C:31]4[C:19](=[CH:20][C:21]=3[S:25][C:24]=2[CH:26]=[CH:27][CH:28]=1)[CH:18]=[C:17]([CH:16]=[O:9])[CH:33]=[CH:32]4

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 90668Benzo(b)naphtho(2,3-d)thiophene, 8-methyl-

Product 1

HCID 14770221HCID 14770221, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a RB flask equipped with magnetic stirring bar, reflux condenser and N2 inlet line with bubbler was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (Aldrich, 38.6 g, 0.119 mol), H2O (100 mL) and CHCl3 (1500 mL). After refluxing the mixture for 15 min, 8-methylbenzo[b]naphtho-[2,3-d]thiophene (Cambridge Chemicals, Inc., 21.0 g, 89.6 mmol) was added to the flask. After refluxing the mixture for 5 h an additional portion of DDQ (19.3 g, 85 mmol) was added. The mixture was then refluxed overnight, cooled and the deep red solution filtered. The solvent was then removed by rotary evaporation and the residual H2O removed by azeotropic distillation with several portions of PhCH3. The material was then dissolved in PhCH3 (500 mL) and applied to a 40×10 cm column of SiO2 and eluted with additional PhCH3 as the solvent. The appropriate fractions were combined and the solvent removed to give 7.12 g of crude material. This was crystallized (PhCH3), filtered and dried to give 5.35 g (22.7% yield) of benzo[b]naphtho[2,3-d]thiophene-8-carbaldehyde, mp 182°-185°, (C,H,S).

Workup

  1. customTo a RB flask equipped with magnetic stirring bar
  2. temperaturereflux condenser and N2 inlet line with bubbler
  3. temperatureAfter refluxing the mixture for 15 min
  4. additionwas added
  5. temperatureThe mixture was then refluxed overnight
  6. temperaturecooled
  7. filtrationthe deep red solution filtered
  8. customThe solvent was then removed by rotary evaporation
  9. customthe residual H2O removed by azeotropic distillation with several portions of PhCH3
  10. dissolutionThe material was then dissolved in PhCH3 (500 mL)
  11. washeluted with additional PhCH3 as the solvent
  12. customthe solvent removed
  13. customto give 7.12 g of crude material
  14. customThis was crystallized (PhCH3)
  15. filtrationfiltered
  16. customdried

Sources & evidence

ORD record
ord-11ae6497d1914e9c9a920a4dd0a5eb34
Source dataset
uspto-grants-1990_04
Patent number
US04918101

Reaction notes

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