4-amino-N,N-diethylbenzene-1-sulfonamide → 2-Phenyl-2-pyridin-4-yl-acetamide

HRID 2186768Notes

Reaction equation

HRID 2186768 reaction equation
[NH2:1]C1C=CC(S(N(CC)CC)(=O)=O)=CC=1.C([O:18][C:19](=O)[CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)C.C[Al](C)C>ClC(Cl)C>[C:27]1([CH:20]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[C:19]([NH2:1])=[O:18])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 950674-amino-N,N-diethylbenzene-1-sulfonamideHCID 12870789Phenyl-pyridin-4-yl-acetic acid ethyl esterHCID 16682925Trimethylaluminum

Product 1

HCID 151332232-Phenyl-2-pyridin-4-yl-acetamideYield 299.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

As described in Example 1, 4-Amino-N,N-diethyl-benzenesulfonamide (242 mg, 1.06 mmol, 2.0 equiv) was coupled with phenyl-pyridin-4-yl-acetic acid ethyl ester (128 mg, 0.53 mmol, 1.0 equiv) using trimethylaluminum (0.53 mL, 0.53 mmol, 2 equiv) in dichloroethane (20 mL). Standard work-up and purification of the residue by rotary chromatography (5% methanol/methylene chloride) provided N-(4-Diethylsulfamoyl-phenyl)-2-phenyl)-2-phenyl-2-pyridin-4-yl-acetamide (337 mg)

Workup

  1. customStandard work-up and purification of the residue by rotary chromatography (5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-e366f688314b4615bd7c67fe68a20105
Source dataset
uspto-grants-2002_06
Patent number
US06407120B1

Reaction notes

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