Aniline → Ethyl 2-(phenylamino)-2-(thiophen-2-yl)acetate

HRID 1044052Notes

Reaction equation

CS(O[CH:6]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>C(#N)C>[C:18]1([NH:17][CH:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-(methylsulfonyloxy)-2-(thiophen-2-yl)acetate (I27) (5.7 g, 21.6 mmol), aniline (2.16 ml, 23.7 mmol) and DIPEA (4.52 ml, 25.9 mmol) were dissolved in acetonitrile (20 ml) to give a yellow solution which was heated under microwave irradiation into a sealed vial at 100° C. for 15 minutes. Conversion complete by UPLC/MS-UV. The solvent was evaporated, and the residue was dissolved in DCM and washed with water and brine, dried (Na2SO4), filtered and evaporated to dryness. The resulting crude was purified by flash chromatography (Petroleum ether/EtOAc=85/15) to get desired compound as a solid (4.33 g, 77% yield).

Workup

customto give a yellow solution which
customThe solvent was evaporated
dissolutionthe residue was dissolved in DCM
washwashed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated to dryness
customThe resulting crude was purified by flash chromatography (Petroleum ether/EtOAc=85/15)

Sources & evidence

ORD record: ord-97190a87af784e6c96c3710904c02779
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563577B2

Reaction notes

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