Thiophene-2-carbohydrazide → HCID 5310124, compound

HRID 715728Notes

Reaction equation

HRID 715728 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][NH2:9])=O.Cl[C:11]1[N:16]=[N:15][C:14]([S:17][CH:18](C)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1>CCCCO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:16]2[N:15]=[C:14]([S:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[CH:12][C:11]2=[N:9][N:8]=1

Participants

4

Reactant 2

HCID 73098Thiophene-2-carbohydrazideHCID 86701044HCID 86701044, compound

Product 1

HCID 5310124HCID 5310124, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
142.5 °C

Procedure

To 2-thiophenecarbohydrazide (215 mg, 1.5 mmol) dissolved in n-BuOH (3 mL) was added ethyl 2-((6-chloropyridazin-3-yl)thio)propanoate (232 mg, 1 mmol), and the whole was heated for 5 h in a 140-145° C. oil bath. The reaction mixture was then cooled to room temperature (˜25° C.), and the solid residue removed by filtration. The filtrate was then diluted with methylene chloride (50 mL), and washed with saturated with NaHCO3 (˜15 mL). The combined aqueous layers were washed twice with methylene chloride, and the organic layers were then combined, washed with brine, dried over MgSO4, filtered, and evaporated. The resulting solid was then recrystallized from EtOH to give ethyl 2-((3-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thio)acetate.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature (˜25° C.)
  2. customthe solid residue removed by filtration
  3. additionThe filtrate was then diluted with methylene chloride (50 mL)
  4. washwashed with saturated with NaHCO3 (˜15 mL)
  5. washThe combined aqueous layers were washed twice with methylene chloride
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting solid was then recrystallized from EtOH

Sources & evidence

ORD record
ord-0cce792853a84361810a32f39a3a735e
Source dataset
uspto-grants-2015_11
Patent number
US09187484B2

Reaction notes

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