Water → 5-[4-(1-Hydroxyethyl)phenyl]-2-nitrothiophene-3-carboxamide

HRID 385726Notes

Reaction equation

HRID 385726 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([N+:15]([O-:17])=[O:16])=[C:12]([C:18]([NH2:20])=[O:19])[CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([N+:15]([O-:17])=[O:16])=[C:12]([C:18]([NH2:20])=[O:19])[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 595260295-(4-Acetylphenyl)-2-nitrothiophene-3-carboxamide

Product 1

HCID 595257315-[4-(1-Hydroxyethyl)phenyl]-2-nitrothiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Acetylphenyl)-2-nitrothiophene-3-carboxamide (0.21 g, 0.723 mmol) was taken up in MeOH (4 mL), followed by the addition of sodium borohydride (0.027 g, 0.723 mmol). The reaction mixture stirred at room temperature for 3 hours. Water was added and the products extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a yellow solid.

Workup

  1. extractionthe products extracted into EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f70ad1fd60414e27a90a0ab4d63d3b9d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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