HCID 86746993, compound → HCID 19755734, compound

HRID 1588374Notes

Reaction equation

HRID 1588374 reaction equation
[N:1]1([B-:10]([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[CH:30]2)([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=[CH:21]2)[N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N:1]1([B-:10]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=[CH:21]2)([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[CH:30]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH2:19]([N+:31]([CH2:30][CH2:24][CH2:23][CH3:28])([CH2:32][CH2:37][CH2:36][CH3:35])[CH2:9][CH2:4][CH2:5][CH3:6])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 1

HCID 86746993HCID 86746993, compound

Product 1

HCID 19755734HCID 19755734, compoundYield 173.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

To a stirred solution of tetrabutylammonium bromide (3.22 g, 10 mmole) in water (25 ml) is added in one portion a solution of sodium tetrakis(1-benzimidazolyl)borate (4.77 g, 10 mmole) in water (40 ml). The mixture is stirred at room temperature for two hours then extracted with methylene chloride (250 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated to obtain pure product (6.26 g, 90%).

Workup

  1. extractionthen extracted with methylene chloride (250 ml)
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-55d8a786c8834a9cbedc20f2ae4657e1
Source dataset
uspto-grants-1993_06
Patent number
US05221761

Reaction notes

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