Potassium Iodide → HCID 17788732, compound

HRID 747661Notes

Reaction equation

HRID 747661 reaction equation
[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH2:12]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20].C(=O)([O-])[O-].[Ca+2].[I-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:1]([O:8][C:9]([NH:10][CH2:11][CH2:12][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10112Calcium CarbonateHCID 133943-CyanophenolHCID 278694benzyl N-(2-bromoethyl)carbamate

Product 1

HCID 17788732HCID 17788732, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

8 g of benzyl-N-(2-bromoethyl)carbamate, 3.7 g of 3-hydroxybenzonitrile, 4.3 g of calcium carbonate, 5.1 g of potassium iodide and 1.1 g of tetrabutylammonium iodide were stirred in dimethylformamide at 60° C. After the treatment with ethyl acetate as the extractant in an ordinary manner, the product was purified by the silica gel column chromatography to obtain 3-[2-(benzyloxycarbonylamino)ethoxy]benzonitrile. Acetic acid containing 20% of hydrogen bromide was added to the product under cooling with ice, and the resultant mixture was stirred at room temperature for 2 hours. The solvent was evaporated, and the residue was washed with ethyl acetate to obtain the title compound.

Workup

  1. customAfter the treatment with ethyl acetate as the extractant in an ordinary manner, the product was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-6f7af63cbcef47f3bdbc78ede8129953
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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