Ethyl Acetate → N-[2-(3-cyanophenoxy)ethyl]-4-(phenylmethanesulfonylamino)benzamide

HRID 747686Notes

Reaction equation

HRID 747686 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)=[O:7])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:31]1([CH2:37][S:38](Cl)(=[O:40])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>CN(C)C=O>[C:18]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:20]=[CH:21][C:2]([NH:1][S:38]([CH2:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:40])=[O:39])=[CH:3][CH:4]=1)#[N:19]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 74740Phenylmethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 177887164-amino-N-[2-(3-cyanophenoxy)ethyl]benzamide

Product 1

HCID 68831603N-[2-(3-cyanophenoxy)ethyl]-4-(phenylmethanesulfonylamino)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

670 mg (2.38 mmol) of 4-amino-N-[2-(3-cyanophenoxy)ethyl]benzamide was dissolved in 10 ml of dimethylformamide. 0.42 ml (2.38 mmol) of diisopropylethylamine and 454 mg (2.38 mmol) of α-toluenesulfonyl chloride were added to the solution at 0° C., and they were stirred for 13 hours. After the treatment with ethyl acetate as the extractant in an ordinary manner, the title compound was obtained.

Sources & evidence

ORD record
ord-ecf10db4e6a142bcab79ba783ebd1773
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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