Triethylamine → 4-(5-Isothiocyanatonaphthalen-2-yloxy)-6,7-dimethoxyquinoline

HRID 1925344Notes

Reaction equation

HRID 1925344 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[S:2].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([NH2:38])=[CH:33][CH:32]=[CH:31]2.CCN(CC)CC>C(Cl)Cl>[N:38]([C:34]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:35]=1[CH:36]=[CH:37][C:28]([O:27][C:18]1[C:17]3[C:22](=[CH:23][C:24]([O:25][CH3:26])=[C:15]([O:14][CH3:13])[CH:16]=3)[N:21]=[CH:20][CH:19]=1)=[CH:29]2)=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11412697Thiocarbonyl diimidazoleHCID 675202746-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Product 1

HCID 860623144-(5-Isothiocyanatonaphthalen-2-yloxy)-6,7-dimethoxyquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thiocarbonyl diimidazole (108 mg, 0.606 mmol) was added to a solution of 6-(6,7-dimethoxyquinolin-4-yloxy)naphthalen-1-amine (210, 0.606 mmol) and NEt3 (84.5 μL, 0.606) in DCM (1.52 mL) in one portion at RT. After 15 minutes of stirring, LCMS and TLC indicated that the reaction was complete. The crude mixture was purified by silica gel chromatography (Hex:EtOAc). MS (ESI, pos. ion) m/z: 389.0 (M+1). Mass Calc'd for C18H15NO3: 388.45.

Workup

  1. customThe crude mixture was purified by silica gel chromatography (Hex:EtOAc)

Sources & evidence

ORD record
ord-f25dd8b6a7b0439db7092a581416ab6f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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