Hydrochloric Acid → 2-(3,4-Dimethoxy-phenyl)-6-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

HRID 532655Notes

Reaction equation

HRID 532655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][C:13]3[CH2:14][C:15]4[C:21]([C:22]5[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=5)=[N:20][N:19](COCC[Si](C)(C)C)[C:16]=4[C:17]=3[CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][C:13]3[CH2:14][C:15]4[C:21]([C:22]5[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=5)=[N:20][NH:19][C:16]=4[C:17]=3[CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866992382-(3,4-Dimethoxy-phenyl)-6-(4-methoxy-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

Product 1

HCID 866992392-(3,4-Dimethoxy-phenyl)-6-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneYield 88.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

2-(3,4-Dimethoxy-phenyl)-6-(4-methoxy-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.39 g, 0.7 mmol) was dissolved in MeOH and treated with concentrated HCl (0.22 mL, 7.3 mmol). The reaction mixture was heated at 100° C. for 4 hr. The solution was cooled to room temperature and the resultant precipitate was filtered, washed with MeOH and concentrated under reduced pressure to provide the corresponding 2-(3,4-Dimethoxy-phenyl)-6-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.25 g, 0.62 mmol) as white solid in 88% yield.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with MeOH
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2c634a5435649bfb72a885d6e4c4c50
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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