1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 59286551, compound

HRID 1876032Notes

Reaction equation

HRID 1876032 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH:24]=[N:23][C:22]([NH2:30])=[CH:21]2>ClCCl.C(OCC)(=O)C.CCCCCC>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH:24]=[N:23][C:22]([N:30]=[C:1]=[S:2])=[CH:21]2

Participants

5

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 59286564HCID 59286564, compound

Product 1

HCID 59286551HCID 59286551, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a stirring solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (142 mg, 0.611 mmol) in dichloromethane (5 mL) was added a suspension of 6-chloro-7-methoxyisoquinolin-3-amine (110 mg, 0.527 mmol) in dichloromethane (5.00 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was applied directly to a silica gel column in 10% ethyl acetate/hexane to yield 106 mg (80%) 6-Chloro-3-isothiocyanato-7-methoxyisoquinoline. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.90 (1H, s), 7.99 (1H, s), 7.36 (1H, s), 7.08 (1H, s), 4.05 (3H, s).

Sources & evidence

ORD record
ord-e01c6c2daaf442f78ce2c00643cd20d2
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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