Bromine → 3-Bromo-6-phenyl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

HRID 532582Notes

Reaction equation

[C:1]1([C:7]2[C:11]3[CH2:12][C:13]4[S:14][CH:15]=[CH:16][C:17]=4[C:10]=3[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]Br>C(O)(=O)C>[Br:18][C:16]1[C:17]2[C:10]3[NH:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]=3[CH2:12][C:13]=2[S:14][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6-Phenyl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.12 g, 0.5 mmol) was added with a solution of bromine in glacial acetic acid (0.5 mL of a 3 M solution). The reaction mixture was heated at 80° C. for 12 hr. The solution was cooled to room temperature and poured into ice water. The resultant precipitate was filtered, washed with water to provide the corresponding 3-Bromo-6-phenyl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.14 g, 0.44 mmol) as yellow solid in 88% yield.

Workup

temperatureThe solution was cooled to room temperature
filtrationThe resultant precipitate was filtered
washwashed with water

Sources & evidence

ORD record: ord-76e621b100d5402fbfeeab06e1d48391
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853207B2

Reaction notes

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