6-Aminoquinoline → 6-Isothiocyanatoquinoline

HRID 512538Notes

Reaction equation

HRID 512538 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[S:2].[N:13]1[C:22]2[C:17](=CC(N)=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[N:8]([C:12]1[CH:11]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:13]=[CH:14][CH:15]=[CH:16]2)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 113736-AminoquinolineHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 137184226-IsothiocyanatoquinolineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Thiocarbonyldiimidazole (740 mg, 4.16 mmol) was added portion-wise to a solution of quinolin-6-amine (0.50 g, 3.47 mmol) in DCM (15 mL) at 0° C., and the mixture was stirred at rt for 1.5 hrs. The reaction mixture was concentrated in vacuo, and the residue was purified by column chromatography eluted with DCM to give 0.60 g (93% yield) of the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography
  3. washeluted with DCM

Sources & evidence

ORD record
ord-476a691517134a6494c45b7d0dbbf943
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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