O,O-Dipyridin-2-yl carbonothioate → 8-Methyl-7-quinolinylisothiocyanate

HRID 2230140Notes

Reaction equation

HRID 2230140 reaction equation
[N:1]([C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)=[C:2]=O.C1C=C(OC(OC2N=CC=CC=2)=[S:23])N=CC=1.NC1C(C)=C2C(C=CC=N2)=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:14][C:13]1[C:4]([N:1]=[C:2]=[S:23])=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2

Participants

6

Reactant 3

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 14115670HCID 14115670, compoundHCID 154343627-Isocyanato8-methylquinoline

Product 1

HCID 120495658-Methyl-7-quinolinylisothiocyanate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

7-Isocyanato8-methylquinoline. To a solution of di-2-pyridyl thionocarbonate (2.29 g) and 4-dimethylaminopyridine (0.02 g) in methylene chloride (50 mL) is added dropwise a solution of 7-amino-8-methylquinoline (1.3 g) in methylene chloride (50 mL). The mixture is stirred for 5 hours at room temperature then rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 25% ethyl acetate/hexanes to afford 8-methyl-7-quinolinylisothiocyanate as a pale yellow solid.

Workup

  1. customThe residue is purified by flash chromatography on silica gel
  2. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bbc9a1aa6acb4a25b65c5364688f4f17
Source dataset
uspto-grants-2002_07
Patent number
US06423724B1

Reaction notes

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