1,1'-Thiocarbonyldiimidazole → 3-Isothiocyanato-4-methylthiophene

HRID 2358167Notes

Reaction equation

HRID 2358167 reaction equation
[NH2:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][CH:3]=1.C1N=CN([C:13](N2C=NC=C2)=[S:14])C=1>O1CCCC1>[CH3:7][C:6]1[C:2]([N:1]=[C:13]=[S:14])=[CH:3][S:4][CH:5]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 57433964-Methylthiophen-3-amine

Product 1

HCID 221398273-Isothiocyanato-4-methylthiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

is obtained by reacting equimolar amounts of 3-amino-4-methylthiophene and N,N′-thiocarbonyldiimidazole in anhydrous tetrahydrofuran (THF) by stirring the reaction mixture at room temperature for 5 hours and then allowing the mixture to stand at room temperature overnight. 4-Methyl-3-thienyl isothiocyanate is isolated by distillative removal of the solvent under reduced pressure using a rotary evaporator, dissolving the residue in ethyl acetate and washing the organic phase repeatedly with water. The organic phase is dried over sodium sulfate and the organic solvent is then distilled off under reduced pressure using a rotary evaporator, giving 4-methyl-3-thienyl isothiocyanate as a brown oily residue. 4-Methyl-3-thienyl isothiocyanate can be used without further purification.

Workup

  1. customis obtained
  2. waitto stand at room temperature overnight

Sources & evidence

ORD record
ord-eb6350147f0c4dfe907269fc31be792f
Source dataset
uspto-grants-2010_07
Patent number
US07763643B2

Reaction notes

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