Methyl 4-methylaminobenzoate → HCID 71238276, compound

HRID 926042

Reaction equation

HRID 926042 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])(=[O:4])=[O:3].[CH3:20][NH:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1>N1C=CC=CC=1>[CH3:29][O:28][C:26]([C:25]1[CH:30]=[CH:31][C:22]([N:21]([CH3:20])[S:2]([C:5]2[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=2)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])(=[O:4])=[O:3])=[CH:23][CH:24]=1)=[O:27]

Participants

4

Reactant 2

HCID 140375Methyl 4-methylaminobenzoateHCID 866763342-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate

Product 1

HCID 71238276HCID 71238276, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.50 g of 2-(trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate, 772 mg of methyl 4-(methylamino)benzoate, and 15 mL of pyridine was stirred at room temperature overnight, and then the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.54 g of 2-(trimethylsilyl)ethyl 3-{[4-(methoxycarbonyl)phenyl](methyl)sulfamoyl}benzoate as a colorless oily substance. ESI+: 450

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4cc60d737d594629af33262fc4c45197
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Linked notes

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