Thiophenol → HCID 22348368, compound

HRID 433164Notes

Reaction equation

HRID 433164 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[N:13]=[C:12]([N:21]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:11]=2[N:10]=[C:9]1[CH2:36][CH2:37][CH2:38][CH3:39])(=O)=O.[C:40]1([SH:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:36]([C:9]1[N:8]([CH2:7][CH2:6][S:46][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:20]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[N:13]=[C:12]([N:21]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[C:11]=2[N:10]=1)[CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 22320423HCID 22320423, compound

Product 1

HCID 22348368HCID 22348368, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A round bottom flask was charged with a magnetic stir bar, 2-{4-[bis(tert-butoxycarbonyl)amino]-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl}ethyl methanesulfonate (0.61 g, 1.08 mmol), benzenethiol (0.21 g, 1.88 mmol), triethylamine (0.25 g, 2.43 mmol) and anhydrous dimethyl formamide (11 mL) under a nitrogen atmosphere. The reaction mixture was heated to 80° C. to give a dark yellow, homogeneous solution that was maintained at 80° C. for 2.5 hours at which time the reaction was judged to be complete. The solution was cooled and then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford a yellow oil. The material was purified by chromatography over silica gel (95/5 dichloromethane/methanol) to provide di(tert-butyl) 2-butyl-1-[2-(phenylthio)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-ylimidodicarbonate (0.54 g, 0.93 mmol) as a light yellow oil. MS (CI) for C32H44N4O4S m/z 581 (MH+), 481, 381, 245.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customto give a dark yellow, homogeneous solution that
  3. temperaturewas maintained at 80° C. for 2.5 hours at which time the reaction
  4. temperatureThe solution was cooled
  5. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  6. customThe layers were separated
  7. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto afford a yellow oil
  12. customThe material was purified by chromatography over silica gel (95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-500280f0df4f4b6ba06b4c16bae16d88
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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