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

HRID 1825905

Reaction equation

HRID 1825905 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

4-Methyl-3-thienyl isothiocyanate 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. b) N-(2-Amino-5-fluorophenyl)-N′-(4-methyl-3-thienyl)thiourea

Workup

  1. waitto stand at room temperature overnight

Sources & evidence

ORD record
ord-3da4e0f2b7a84f2180fee1f21991edc2
Source dataset
uspto-grants-2006_05
Patent number
US07049333B2

Linked notes

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