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

HRID 532652Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2,6-Bis-(4-methoxy-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.11 g, 0.2 mmol) was dissolved in MeOH and treated with concentrated HCl (0.06 mL, 2.0 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 2,6-Bis-(4-methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.08 g, 0.19 mmol) as white solid in 95% yield.

Workup

temperatureThe solution was cooled to room temperature
filtrationthe resultant precipitate was filtered
washwashed with MeOH
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d130b391e2d14d2f8405163ca04741a7
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853207B2

Reaction notes

Loading…