Benzyl Isothiocyanate → 4-Benzyl-1-(thiophene-2-carbonyl)thiosemicarbazide

HRID 229757

Reaction equation

HRID 229757 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][NH2:9])=[O:7].[CH2:10]([N:17]=[C:18]=[S:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[CH2:10]([NH:17][C:18]([NH:9][NH:8][C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:7])=[S:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 73098Thiophene-2-carbohydrazide

Product 1

HCID 52606884-Benzyl-1-(thiophene-2-carbonyl)thiosemicarbazideYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a hot solution of 2-thiophencarboxylic acid hydrazide (5.0 g, 35 mmol) in acetonitrile (80 mL) was added neat benzyl isothiocyanate (4.7 mL, 35 mmol) via syringe. When the solvent started to boil, the reaction vessel was removed from the heat source and allowed to cool to room temperature. The resulting crystals were collected by vacuum filtration, washed with diethyl ether and air-dried to yield N-benzyl-2-(thien-2-ylcarbonyl)hydrazinecarbothioamide (9.11 g; 89%; (M+H)+−292.2).

Workup

  1. customthe reaction vessel was removed from the heat source
  2. filtrationThe resulting crystals were collected by vacuum filtration
  3. washwashed with diethyl ether
  4. customair-dried

Sources & evidence

ORD record
ord-af782016dd43493eba98f290432a7005
Source dataset
uspto-grants-2009_07
Patent number
US07563905B2

Linked notes

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