4-Chloro-1-(2-thienyl)butan-1-one → 2-[4-Chloro-1-(thiophen-2-yl)-butylidene]-hydrazinecarbothioamide

HRID 613685

Reaction equation

HRID 613685 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH:6]1[CH:10]=[C:9]([C:11]([CH2:13][CH2:14][CH2:15][Cl:16])=O)[S:8][CH:7]=1>CO.Cl.O>[Cl:16][CH2:15][CH2:14][CH2:13][C:11](=[N:1][NH:2][C:3](=[S:4])[NH2:5])[C:9]1[S:8][CH:7]=[CH:6][CH:10]=1

Participants

6

Reactant 2

HCID 1235114-Chloro-1-(2-thienyl)butan-1-oneHCID 2723789Thiosemicarbazide

Product 1

HCID 545696092-[4-Chloro-1-(thiophen-2-yl)-butylidene]-hydrazinecarbothioamideYield 57%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Thiosemicarbazide (9.11 g, 0.1 mol) was added under nitrogen to a solution 4-chloro-2'-butyrothienone (16.2 mL, 0.1 mol) in 350 mL of methanol plus 27 mL 1N HCl plus 25 mL of water. After stirring at room temperature for approximately 2 hours, all of the solid had dissolved. The reaction was then stirred at room temperature for 24 hours (overnight). By TLC starting material remained. An additional 27 mL of 1N HCl was added and the reaction stirred at room temperature for 6 hours. The solid formed was removed by filtration and dried under high vacuum to give 14.87 g (57%) of the title compound as a brown solid, mp 120-122° C.

Workup

  1. dissolutionall of the solid had dissolved
  2. stirringThe reaction was then stirred at room temperature for 24 hours (overnight)
  3. stirringthe reaction stirred at room temperature for 6 hours
  4. customThe solid formed
  5. customwas removed by filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-08f667f3cc214dae90b9d0e45627e7c1
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Linked notes

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