Hydrochloric Acid → [4-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenyl]-(4-methoxy-ph enyl)-amine

HRID 532548Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

(4-Methoxy-phenyl)-{4-[4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl]-phenyl}-amine (0.24 g, 0.5 mmol) was dissolved in MeOH and treated with concentrated HCl (0.16 mL, 5 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 [4-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenyl]-(4-methoxy-ph enyl)-amine (0.14 g, 0.40 mmol) as brown solid in 80% 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-4c46e4c6b2e14083bd7bccfbf5e1cce7
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853207B2

Reaction notes

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