Methyl isothiocyanate → 2-Thiophenecarboxylic acid, 2-[(methylamino)thioxomethyl]hydrazide

HRID 1199371Notes

Reaction equation

HRID 1199371 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][NH2:9])=[O:7].[CH3:10][N:11]=[C:12]=[S:13]>C1COCC1>[C:2]1([C:6]([NH:8][NH:9][C:12]([NH:11][CH3:10])=[S:13])=[O:7])[S:1][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 73098Thiophene-2-carbohydrazide

Product 1

HCID 28198722-Thiophenecarboxylic acid, 2-[(methylamino)thioxomethyl]hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred mixture of 2-thiophene carboxylic acid hydrazide (4.75 g, 3.34×10-2 mole) and THF (115 ml) was warmed with a heat gun until homogeneous. A solution of freshly distilled methyl isothiocyanate (2.56 g, 3.51×10-2 mole) and THF (5 ml) was then added dropwise. After being stirred for about 14 hours the precipitate was collected by filtration, washed with a little Et2O, and dried by suction affording a colorless powder: 7.1 g (99%).

Workup

  1. temperaturewas warmed with a heat gun until homogeneous
  2. filtrationwas collected by filtration
  3. washwashed with a little Et2O
  4. customdried by suction
  5. customaffording a colorless powder

Sources & evidence

ORD record
ord-d8e19dfd0977460ba55b2853814e137e
Source dataset
uspto-grants-1990_02
Patent number
US04900743

Reaction notes

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