Hydrochloric Acid → HCID 20377700, compound

HRID 1703481Notes

Reaction equation

HRID 1703481 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[S:5]1[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[CH:7]=[C:6]1[C:13]([O-:15])=[O:14].Cl[C:17]([C:19]1[CH:20]=[C:21]([CH2:25][C:26]#[N:27])[CH:22]=[CH:23][CH:24]=1)=[O:18].Cl.[CH2:29](Cl)Cl>>[CH3:29][O:14][C:13]([C:6]1[S:5][C:9]2[S:10][C:11]([C:17]([C:19]3[CH:20]=[C:21]([CH2:25][C:26]#[N:27])[CH:22]=[CH:23][CH:24]=3)=[O:18])=[CH:12][C:8]=2[CH:7]=1)=[O:15]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 6933376HCID 6933376, compoundHCID 20377681HCID 20377681, compound

Product 1

HCID 20377700HCID 20377700, compound

Conditions

Temperature
20 °C

Procedure

Anhydrous aluminium chloride (167.5 g) is added in small portions over a period of 11/2 hours to a mixture of methyl (thieno[2,3-b]thiophene-2-carboxylate (49.5 g) and 3-chloroformyl-phenylacetonitrile (44.8 g) in methylene chloride (1250 cc) at 20°-30° C. The reaction mixture is stirred for 17 hours at a temperature of about 20° C., then hydrolysed, with care, by the slow addition of an N aqueous solution of hydrogen chloride (500 cc), the internal temperature being kept at about 20° C. by external cooling with an ice bath. The aqueous phase is decanted off and extracted three times with methylene chloride (total 600 cc). The combined methylene chloride solutions are washed three times with distilled water (total 240 cc), dried over anhydrous sodium sulphate in the presence of decolourizing charcoal (2 g), filtered and evaporated. The residue is taken up in boiling acetonitrile (250 cc). After cooling for 1 hour at 4° C., the resulting crystals are filtered off, washed three times with iced acetonitrile (total 60 cc), and dried under reduced pressure (20 mm Hg) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. 3-(5-Methoxycarbonyl-thieno[2,3-b]thien-2-yl)carbonyl-phenylacetonitrile (74.7 g), melting at 184° C., is thus obtained.

Workup

  1. custombeing kept at about 20° C.
  2. temperatureby external cooling with an ice bath
  3. customThe aqueous phase is decanted off
  4. extractionextracted three times with methylene chloride (total 600 cc)
  5. washThe combined methylene chloride solutions are washed three times with distilled water (total 240 cc)
  6. dry with materialdried over anhydrous sodium sulphate in the presence of decolourizing charcoal (2 g)
  7. filtrationfiltered
  8. customevaporated
  9. temperatureAfter cooling for 1 hour at 4° C.
  10. filtrationthe resulting crystals are filtered off
  11. washwashed three times with iced acetonitrile (total 60 cc)
  12. dry with materialdried under reduced pressure (20 mm Hg) at a temperature of about 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-cb675e392d8b462ba919768cec42f57c
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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