Sodium hydride → (2-Iodobenzenesulfonyl)-11,12-dihydro-11,12-diazaindeno[2,1-a]fluorene

HRID 531893Notes

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.[H-].[Na+].[I:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30](Cl)(=[O:32])=[O:31]>C1COCC1>[I:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([C: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[NH:19][C:18]1[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:32])=[O:31]

Participants

Conditions

Temperature: 40 °C

Procedure

43 g (169 mmol) of 11,12-dihydroindolo[2,3-a]carbazole are initially introduced in 1000 ml of THF, and 8.9 g (223.3 mmol) of NaH (60% in oil) are added at 0° C. 24 g (80 mmol) of 2-iodobenzenesulfonyl chloride are subsequently added to the mixture, which is then stirred at 40° C. for 12 h. 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: 29 g (574 mmol), 72% of theory, purity according to HPLC 99.9%.

Workup

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-08223aaff67c4ab39b602228fb37d24d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09356243B2

Reaction notes

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