Water → 3-[7-bromo-2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl]propyl acetate

HRID 415530Notes

Reaction equation

HRID 415530 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][C:16]([Br:21])=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[NH:10][C:9]1=[S:22])(=[O:3])[CH3:2].O.[OH-].[NH4+].I[CH3:27]>C(O)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][C:16]([Br:21])=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[S:22][CH3:27])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14923Ammonium HydroxideHCID 866337413-(7-bromo-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propyl acetate

Product 1

HCID 666201743-[7-bromo-2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl]propyl acetateYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round-bottomed flask containing 3-(7-bromo-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propyl acetate (28.9 g, 76.0 mmol) was added water (180 mL), ethanol (180 mL), and ammonium hydroxide (38 mL). The resulting suspension was stirred at ambient temperature. To this suspension was added iodomethane (9.5 mL, 152 mmol), and the reaction was stirred for 2 h. The suspension was filtered through a sintered glass funnel and the residue was washed with diethyl ether and dried under reduced pressure to afford 3-[7-bromo-2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl]propyl acetate (22.2 g) as tan solid.

Workup

  1. stirringthe reaction was stirred for 2 h
  2. filtrationThe suspension was filtered through a sintered glass funnel
  3. washthe residue was washed with diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-a9cad312dd36445c823dc6c5b534a8ba
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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