Sodium methanethiolate → HCID 22320459, compound

HRID 433197Notes

Reaction equation

HRID 433197 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1[CH3:22].[CH3:23][S-:24].[Na+]>CN(C)C=O>[CH3:22][C:9]1[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:24][CH3:23])[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 22320416HCID 22320416, compound

Product 1

HCID 22320459HCID 22320459, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

1-(6-Chlorohexyl)-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (2.5 g, 8 mmol), sodium thiomethoxide (1.13 g, 15.5 mmol) and N,N-dimethylformamide (15 mL) were combined and heated at 160° C. for 3 hours. The reaction was quenched with water and the precipitate isolated to provide 1.5 g of 2-methyl-1-[6-(methylthio)hexyl]-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. customThe reaction was quenched with water
  2. customthe precipitate isolated

Sources & evidence

ORD record
ord-da34fed10cfc40f8a8b5af860d6178e7
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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