Hydrochloric Acid → HCID 53908312, compound

HRID 235095Notes

Reaction equation

HRID 235095 reaction equation
[CH:1]1([C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].O.NN.Cl>C(O)COCCO.O>[CH:1]1([CH2:6][C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 10219686Cyclopentyl-2-thienylmethanone

Product 1

HCID 53908312HCID 53908312, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

The material from step 33a above (12.28 g ) was dissolved in 100 mL of diethylene glycol. KOH (11.20 g, 200 mmol) was added and dissolved. Hydrazine hydrate (8.25 mL, 170 mmol) was added, and the reaction was heated to gentle reflux for 18 hours. After cooling, the reaction was diluted with water, neutralized with 66 mL of 3 N HCl and extracted with 3×100 mL of hexane. The extract was dried over MgSO4, filtered through a pad of silica gel and evaporated on a rotary evaporator to give 6.58 g of the title product. NMR (CDCl3) δ:1.21 (m, 2H), 1.61 (m, 4H), 1.81 (m, 2H), 2.14 (septet, 1H), 2.81 (d, 2H), 6.79 (dd, J=4 Hz, 1H), 6.91 (dd, J=4, 5 Hz, 1H), 7.11 (dd, J=1, 5 Hz, 1H).

Workup

  1. dissolutiondissolved
  2. temperaturethe reaction was heated
  3. temperatureto gentle reflux for 18 hours
  4. temperatureAfter cooling
  5. extractionextracted with 3×100 mL of hexane
  6. dry with materialThe extract was dried over MgSO4
  7. filtrationfiltered through a pad of silica gel
  8. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-b93bab1678234cf1bf8fbb60839ad4d8
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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