Triethylamine → 2-Isothiocyanato-7-methoxyquinoxaline

HRID 250063Notes

Reaction equation

HRID 250063 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([N:14]=[CH:15][C:16]([NH2:20])=[N:17]2)=[CH:12][CH:11]=1.C(N(CC)CC)C.[C:28](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:29]>C(Cl)Cl>[N:20]([C:16]1[CH:15]=[N:14][C:13]2[C:18](=[CH:19][C:10]([O:9][CH3:8])=[CH:11][CH:12]=2)[N:17]=1)=[C:28]=[S:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 667246317-Methoxyquinoxalin-2-amine 2,2,2-trifluoroacetate

Product 1

HCID 574765692-Isothiocyanato-7-methoxyquinoxalineYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-methoxyquinoxalin-2-amine 2,2,2-trifluoroacetate (578 mg, 2 mmol), triethylamine (335 μL, 2.400 mmol), and 1,1′-thiocarbonyldipyridin-2(1 H)-one (557 mg, 2.400 mmol) was stirred in 5 mL DCM for 24 h. The reaction was directly eluted on a 120 g silica gel cartridge with 0 to 25% EtOAc in hexane, 25 min, at 35 mL/min to afford 2-isothiocyanato-7-methoxyquinoxaline (84 mg, 0.387 mmol, 19% yield).

Workup

  1. washThe reaction was directly eluted on a 120 g silica gel cartridge with 0 to 25% EtOAc in hexane, 25 min, at 35 mL/min

Sources & evidence

ORD record
ord-d6cd042068f24901bbff670be897a06e
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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