Chloroform → HCID 22921204, compound

HRID 1377216Notes

Reaction equation

HRID 1377216 reaction equation
[N+:1]([C:4]1[CH:49]=[CH:48][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][C:31]5[CH:36]=[CH:35][C:34]([C:37](=O)[C:38]6[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=6)=[CH:33][CH:32]=5)=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([SiH](CC)CC)C.ClC(Cl)C.C(Cl)(Cl)Cl>ClCCl>[N+:1]([C:4]1[CH:49]=[CH:48][C:7]([CH2:8][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][C:31]5[CH:36]=[CH:35][C:34]([CH2:37][C:38]6[CH:39]=[CH:40][C:41]([N+:44]([O-:46])=[O:45])=[CH:42][CH:43]=6)=[CH:33][CH:32]=5)=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 63651,1-DichloroethaneHCID 12052TriethylsilaneHCID 22920878HCID 22920878, compound

Product 1

HCID 22921204HCID 22921204, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 1-liter four-necked flask equipped with a stirring device, a thermometer, a condenser and a nitrogen substituting device, 17.7 g of 1,1-bis(4-(4-(4-nitrobenzoyl)phenylmethyl) phenyl)methane was dissolved in 150 milliliters of dichloromethane, 14.5 g of triethylsilane and 20.7 g of boron trifluoride ethyl ether complex were added, and they were stirred for 20 hours at reflux of dichloroethane. After the end of the reaction was confirmed by a liquid chromatography, the reaction solution was cooled to room temperature, poured in 100 milliliters of ice water, and then 150 milliliters of chloroform was added for extraction. Thereafter, the solution was washed with a 6N-HCl aqueous solution of from 50° to 55° C., an aqueous solution of sodium hydrogencarbonate, brine and water, removed off chloroform and dichloroethane by a rotary evaporator, and then recrystallized from a chloroform solvent, to obtain 16.4 g of 1,1-bis(4-(4-(4-nitrophenylmethyl)phenylmethyl)phenyl)methane as crystals.

Workup

  1. customIn a 1-liter four-necked flask equipped with a stirring device
  2. washThereafter, the solution was washed with a 6N-HCl aqueous solution of from 50° to 55° C.
  3. customan aqueous solution of sodium hydrogencarbonate, brine and water, removed off chloroform and dichloroethane
  4. customby a rotary evaporator
  5. customrecrystallized from a chloroform solvent

Sources & evidence

ORD record
ord-87797ada8155495ca58589a0bf066fc9
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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