Aniline → 2-(Benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acid

HRID 469458Notes

Reaction equation

HRID 469458 reaction equation
[S:1]1[CH:5]=[C:4](B(O)O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.O=[CH:22][C:23]([OH:25])=[O:24]>C(#N)C>[S:1]1[CH:5]=[C:4]([CH:22]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:23]([OH:25])=[O:24])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

5

Reactant 3

HCID 6115AnilineHCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 585569682-(Benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acidYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Benzo[b]thiophen-3-ylboronic acid (387 mg, 2.17 mmol), aniline (202 mg, 2.17 mmol), and 2-oxoacetic acid hydrate (200 mg, 2.17 mmol) were dissolved in acetonitrile (12 ml) and then stirred at 100° C. under microwave irradiation for 1 hour. The solvent was evaporated, and the residue was dissolved in EtOAc and washed with sat.NaHCO3. 2N HCl was added to the aqueous phase until pH was about 7, and the product was extracted with EtOAc. The organic phase was dried with Na2SO4, filtered and evaporated to obtain 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acid (295 mg, 48% yield).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed
  4. addition2N HCl was added to the aqueous phase until pH was about 7
  5. extractionthe product was extracted with EtOAc
  6. dry with materialThe organic phase was dried with Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d12fd20f0e5e4e09bc166e5d75985e87
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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