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

HRID 532646Notes

Reaction equation

HRID 532646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH2:11][C:12]4[C:18]([C:19]5[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=5)=[N:17][N:16](COCC[Si](C)(C)C)[C:13]=4[C:14]=3[CH:15]=2)=[CH:4][CH:3]=1.Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH2:11][C:12]4[C:18]([C:19]5[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=5)=[N:17][NH:16][C:13]=4[C:14]=3[CH:15]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866992352-(4-Fluoro-phenyl)-6-(4-methoxy-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

Product 1

HCID 718151692-(4-Fluoro-phenyl)-6-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

2-(4-Fluoro-phenyl)-6-(4-methoxy-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.62 g, 0.12 mmol) was dissolved in MeOH and treated with concentrated HCl (0.37 mL, 1.2 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-(4-Fluoro-phenyl)-6-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a ]pentalene (0.26 g, 0.09 mmol) as brown solid in 75% 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-96d7ebd1ea074c6181541d850e15fbfd
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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