1,1'-Thiocarbonyldiimidazole → HCID 22139828, compound

HRID 2250506Notes

Reaction equation

HRID 2250506 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[S:2].NC1[C:18]([Cl:19])=[CH:17][S:16]C=1>C1COCC1>[Cl:19][C:18]1[C:12]([N:8]=[C:1]=[S:2])=[CH:11][S:16][CH:17]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 221398234-Chlorothiophen-3-amine

Product 1

HCID 22139828HCID 22139828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.46 g of thiocarbonyldiimidazole are added to a solution of 1.1 g of 3-amino-4-chlorothiophene in 20 ml of anhydrous THF, and the mixture is stirred at room temperature for one hour. The solid is distilled off under reduced pressure, the residue is dissolved in ethyl acetate, the organic phase is treated twice with water in a separating funnel and then dried, and the solvent is again distilled off under reduced pressure. This gives 4-chloro-3-thienyl isothiocyanate as a dark oil which is then reacted further without further purification steps.

Workup

  1. distillationThe solid is distilled off under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. additionthe organic phase is treated twice with water in a separating funnel
  4. customdried
  5. distillationthe solvent is again distilled off under reduced pressure
  6. customThis gives 4-chloro-3-thienyl isothiocyanate as a dark oil which is then reacted further without further purification steps

Sources & evidence

ORD record
ord-f36ebc2000d845b58dfcb3f7f2894d27
Source dataset
uspto-grants-2008_01
Patent number
US07317033B2

Reaction notes

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