2-Dimethylaminopyridine → HCID 18979047, compound

HRID 1901475Notes

Reaction equation

HRID 1901475 reaction equation
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[C:13]#[N:14].C1C=C(O[C:23](OC2N=CC=CC=2)=[S:24])N=CC=1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:13]([C:5]1[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=[C:2]([N:1]=[C:23]=[S:24])[C:3]=2[CH3:15])[N:8]=[CH:7][CH:6]=1)#[N:14]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 18979044HCID 18979044, compound

Product 1

HCID 18979047HCID 18979047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-amino-4-cyano-5,8-dimethylquinoline (2.0 g, 10.15 mmol), di-2-pyridyl thionocarbonate (2.52 g, 10.86 mmol), dimethylaminopyridine (0.266 g, 2.18 mmol) and methylene chloride (62 mL) is stirred at room temperature for 1.5 hours. Evaporation affords a residue which is purified by chromatography through a short column consisting of layers of sand/flash silica gel/sand, using methylene chloride as eluent, to give 4-cyano-5,8-dimethyl-6-isothiocyanatoquinoline.

Workup

  1. customEvaporation
  2. customaffords a residue which
  3. customis purified by chromatography through a short column

Sources & evidence

ORD record
ord-9910176ba47f4d569694b0b44e2e89e9
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

Loading…