Water → HCID 86604116, compound

HRID 1181579Notes

Reaction equation

HRID 1181579 reaction equation
[CH3:1][S:2][C:3]([S:30][CH3:31])=[CH:4][C:5]([C:7]1[N:23](C2CCCCO2)[C:10]2=[CH:11][C:12]3[C:13]([CH3:22])([CH3:21])[C:14](=[O:20])[N:15]([CH2:18][CH3:19])[C:16]=3[CH:17]=[C:9]2[N:8]=1)=[O:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[CH3:31][S:30][C:3]([S:2][CH3:1])=[CH:4][C:5]([C:7]1[NH:23][C:10]2=[CH:11][C:12]3[C:13]([CH3:21])([CH3:22])[C:14](=[O:20])[N:15]([CH2:18][CH3:19])[C:16]=3[CH:17]=[C:9]2[N:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 962Water2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 11583444HCID 11583444, compound

Product 1

HCID 86604116HCID 86604116, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 2-(3,3-bis-methylsulfanyl-acryloyl)-5-ethyl-7,7-dimethyl-1-(tetrahydro-pyran-2-yl)-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (2.25 g, 4.9 mmol) and p-toluenesulfonic acid monohydrate (0.5 g, 2.6 mmol) was dissolved in methanol (25 mL) and water (3 mL) and stirred at reflux for 3 h. After cooling to room temperature, water (50 mL) was added and the mixture extracted with etyhl acetate (3×50 mL). The combined organic layers were washed with water and concentrated in vacuo. The crude product was recrystallized from methanol to yield 2-(3,3-bis-methylsulfanyl-acryloyl)-5-ethyl-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (0.71 g, 39%) as yellow solid.

Workup

  1. temperatureat reflux for 3 h
  2. extractionthe mixture extracted with etyhl acetate (3×50 mL)
  3. washThe combined organic layers were washed with water
  4. concentrationconcentrated in vacuo
  5. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-5d73a3e272634bdb93802151d8725537
Source dataset
uspto-grants-2007_10
Patent number
US07285569B2

Reaction notes

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