Diethylene Glycol → HCID 21943885, compound

HRID 1868542Notes

Reaction equation

HRID 1868542 reaction equation
[CH3:1][C:2]1[S:14][C:5]2[C:6](=O)[C:7]3[S:8][C:9]([CH3:12])=[CH:10][C:11]=3[C:4]=2[CH:3]=1.C(O)COCCO.O.NN.[OH-].[K+]>O>[CH3:12][C:9]1[S:8][C:7]2[CH2:6][C:5]3[S:14][C:2]([CH3:1])=[CH:3][C:4]=3[C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 23635837HCID 23635837, compound

Product 1

HCID 21943885HCID 21943885, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 45 g (205 mmol) of 2,5-dimethyl-7H-thieno[3′,2′:3,4]cyclopenta[1,2-b]thiophen-7-one, 600 mL of diethylene glycol and 70 mL of hydrazine monohydrate was placed into the bulb. The mixture was warmed to 80° C. and kept at this temperature in 1 h at stirring. Then the mixture was intensively refluxed in 1 h, cooled to r.t. treated with solution of 70 g KOH in 230 mL of water. The resulting mixture was carefully heated and the gas started to bubble. The mixture was refluxed for 2 hours, then it was cooled to 70-80° C. and poured into 3 L water. The precipitate was decanted, filtered, washed 7 times with 200-300 mL of water and dried. Yield 32 g (78%).

Workup

  1. temperatureThen the mixture was intensively refluxed in 1 h
  2. temperaturecooled to r.t.
  3. temperatureThe resulting mixture was carefully heated
  4. customto bubble
  5. temperatureThe mixture was refluxed for 2 hours
  6. temperatureit was cooled to 70-80° C.
  7. additionpoured into 3 L water
  8. customThe precipitate was decanted
  9. filtrationfiltered
  10. washwashed 7 times with 200-300 mL of water
  11. customdried

Sources & evidence

ORD record
ord-447363c4e9c74dd2b9ce36c72d4efa7d
Source dataset
uspto-grants-2009_12
Patent number
US07635781B2

Reaction notes

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