Benzenamine, 3-(methylthio)- → (3-Methylsulfanyl-phenylamino)-phenyl-acetic acid ethyl ester

HRID 76990

Reaction equation

HRID 76990 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:14][S:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].CCN(C(C)C)C(C)C>C(#N)C>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[C:16]([S:15][CH3:14])[CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7]

Participants

5

Reactant 3

HCID 15693Benzenamine, 3-(methylthio)-HCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 59401206(3-Methylsulfanyl-phenylamino)-phenyl-acetic acid ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 2-bromo-2-phenylacetate (0.22 mL, 1.23 mmol), 3-(methylthio)aniline (0.22 mL, 1.85 mmol), and DIPEA (0.32 mL, 1.85 mmol) are dissolved in acetonitrile (3 mL) and heated under microwave irradiation at 100° C. for 1 hour. Acetonitrile is evaporated and the crude residue is purified by flash chromatography (petroleum ether/EtOAc=85/15) to obtain intermediate I98 as a colorless oil (292 mg, 79% yield).

Workup

  1. customAcetonitrile is evaporated
  2. customthe crude residue is purified by flash chromatography (petroleum ether/EtOAc=85/15)

Sources & evidence

ORD record
ord-762ebd227668498f986026cf8361e129
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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