Acetic Acid → HCID 33777858, compound

HRID 2420787Notes

Reaction equation

HRID 2420787 reaction equation
[C:1]([CH:3]1[CH2:7][S:6](=O)[CH2:5][CH2:4]1)#[N:2].C(O)(=O)C.O.[NH2:14][NH2:15]>C(O)C>[NH:14]1[C:4]2[CH2:5][S:6][CH2:7][C:3]=2[C:1]([NH2:2])=[N:15]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 53410103HCID 53410103, compound

Product 1

HCID 33777858HCID 33777858, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1.00 g (7.86 mmol) of 4-cyanotetrahydrothiophenone in 6 mL of ethanol was added 0.275 mL (286 mg, 4.76 mmol) of glacial acetic acid, followed by 0.475 mL (489 mg, 9.77 mmol) of hydrazine hydrate. The resulting clear solution was stirred overnight under nitrogen with heating in an oil bath at 80° C. The cooled reaction mixture was then partitioned between ethyl acetate and saturated sodium bicarbonate aqueous solution. The aqueous phase was re-extracted with an additional portion of ethyl acetate. The combined organic fractions were washed with saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate, filtered, and concentrated to a syrup. Trituration of this oil with dichloromethane containing a small amount (less than 3%) of methanol resulted in crystallization. The suspension was heated to gentle reflux for a few minutes and then cooled. The solid was collected on a filter and washed with a small volume of dichloromethane to yield the title compound as almost colorless crystals. LC-MS 142 (M+1).

Workup

  1. customThe cooled reaction mixture
  2. customwas then partitioned between ethyl acetate and saturated sodium bicarbonate aqueous solution
  3. extractionThe aqueous phase was re-extracted with an additional portion of ethyl acetate
  4. washThe combined organic fractions were washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a syrup
  8. customTrituration of this oil with dichloromethane containing a small amount (less than 3%) of methanol resulted in crystallization
  9. temperatureThe suspension was heated
  10. temperatureto gentle reflux for a few minutes
  11. temperaturecooled
  12. customThe solid was collected on
  13. filtrationa filter
  14. washwashed with a small volume of dichloromethane

Sources & evidence

ORD record
ord-bb3547642c8043b1a60bfba35dd18e50
Source dataset
uspto-grants-2011_06
Patent number
US07956061B2

Reaction notes

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