Sodium Hydroxide → HCID 178517407, compound

HRID 1992312Notes

Reaction equation

HRID 1992312 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[N:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH2:17])=[O:16])=O.[OH-].[Na+]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:17]=[C:15]([OH:16])[C:14]2[CH:18]=[CH:19][CH:20]=[N:21][C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 591303732-[(1-Benzothien-2-ylcarbonyl)amino]nicotinamide

Product 1

HCID 178517407HCID 178517407, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(1-benzothien-2-ylcarbonyl)amino]nicotinamide (0.3 g, 1.0 mmol) in ethanol (20 mL) was added NaOH (10 N, 0.3 mL, 3.0 mmol). The resulting solution was heated to reflux overnight. On cooling to rt the solvent was removed under reduced pressure. The residue was dissolved in excess of water and acidified with HCl. The resulting precipitate was filtered and washed with water to afford the product as yellow powder (0.16 g, 57%). HPLC/MS: (M+H)+ 280.0 m/z; Retention time (LC-MS)=2.66 min; 1H NMR (DMSO-D6): 13.17 (1H, s); 8.94(1H, m); 8.61(1H, s); 8.50(1H, d); 8.08(1H, d); 7.97(1H, d); 7.52(3H, m).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight
  3. customwas removed under reduced pressure
  4. dissolutionThe residue was dissolved in excess of water
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-7d9675886c3f489ea8657ad0d965426d
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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