Potassium Carbonate → 2-(12H-11,12-diazaindeno[2,1-a]fluoren-11-yl)benzenethiol

HRID 76378Notes

Reaction equation

[CH:1]1[C:6]2[NH:7][C:8]3[C:9](=[CH:10][CH:11]=[C:12]4[C:20]=3[NH:19][C:18]3[C:13]4=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[SH:28].C([O-])([O-])=O.[K+].[K+]>C(OCCCC)CCC.[Cu].[Cu]I>[CH:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[C:6]=1[NH:7][C:8]1[C:9]2=[CH:10][CH:11]=[C:12]2[C:20]=1[N:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[SH:28])[C:18]1[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 144 °C

Procedure

25 g (96.6 mmol) of 11,12-dihydroindolo[2,3-a]carbazole are added to 12.5 g (48 mmol) of 2-iodobenzenethiol in 80 ml of di-n-butyl ether, and the solution is degassed. 6.6 g (0.105 mmol) of copper powder, 0.92 g (0.003 mmol) of copper(I) iodide and 14.6 g (106.6 mmol) of K2CO3 are subsequently added to the mixture, which is then stirred at 144° C. under protective gas for 4 days. The organic phase is dried over MgSO4, and the solvent is removed in vacuo. The residue is recrystallised from acetone and finally sublimed in a high vacuum. Yield: 22.5 g (61 mmol), 66% of theory, purity according to HPLC 89.4%.

Workup

customthe solution is degassed
dry with materialThe organic phase is dried over MgSO4
customthe solvent is removed in vacuo
customThe residue is recrystallised from acetone

Sources & evidence

ORD record: ord-f489abe5d66d492f968304771aaa5ff1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835626B2

Reaction notes

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