Reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[C:18]1([S-:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na+]>CS(C)=O>[C:18]1([S:24][CH2:2][CH2:3][N:4]2[C:16]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]=[C:8]([NH2:17])[C:7]=3[N:6]=[CH:5]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
A round bottom flask was charged with a magnetic stir bar, 1-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 8.11 mmol), sodium benzenethiolate (1.79 g, 12.16 mmol), and anhydrous dimethyl sulfoxide (40 mL) under a nitrogen atmosphere. The reaction mixture was heated to 100° C. to give a homogeneous solution that was maintained at 100° C. for 30 minutes at which time the starting material was completely consumed. The hot solution was poured into rapidly stirred water (300 mL) which caused a solid to precipitate out of solution. The solid was collected by filtration to afford an off-white solid. The material was triturated with acetonitrile and collected by filtration to give 1-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (2.08 g, 6.49 mmol) as an off-white powder, m. p. 233-235° C.
Workup
- additionA round bottom flask was charged with a magnetic stir bar
- customto give a homogeneous solution that
- temperaturewas maintained at 100° C. for 30 minutes at which time the starting material
- customwas completely consumed
- additionThe hot solution was poured into rapidly stirred water (300 mL) which
- customto precipitate out of solution
- filtrationThe solid was collected by filtration
- customto afford an off-white solid
- customThe material was triturated with acetonitrile
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-22722c7e1fc6447ab4a0779d67d74c3e
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921826B2
Linked notes
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