Sodium Hydroxide → (2-Amino-5-phenyl-thiophen-3-yl)-phenyl-methanone

HRID 133547Notes

Reaction equation

HRID 133547 reaction equation
[C:1]([C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:11][C:10]=1[NH:20]C(=O)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[NH4+].[Cl-]>CCO>[NH2:20][C:10]1[S:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:13][C:9]=1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 68895390N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide

Product 1

HCID 28325476(2-Amino-5-phenyl-thiophen-3-yl)-phenyl-methanoneYield 132%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 0.393 g (1.22 mmol) of N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide in 15 ml EtOH was added 2.5 ml of aq. NaOH (4N). The reaction mixture stirred at RT for 1 hour, and then poured onto an aq. solution of NH4Cl sat. and the product was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to yield 0.45 g (98%) of (2-amino-5-phenyl-thiophen-3-yl)-phenyl-methanone as a light brown solid. ES-MS m/e (%): 280 (M+H+, 100).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d82832b4fd2421a9309b6c08f09532f
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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