N-(pyrazin-2-ylcarbamothioyl)benzamide → N-Pyrazinylthiourea

HRID 1715229Notes

Reaction equation

HRID 1715229 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([NH:10]C(=O)C1C=CC=CC=1)=[S:9]>[OH-].[Na+]>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([NH2:10])=[S:9]

Participants

3

Reactant 1

HCID 14460677N-(pyrazin-2-ylcarbamothioyl)benzamide

Product 1

HCID 2771013N-Pyrazinylthiourea

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-[(pyrazin-2-ylamino) carbonothioyl]benzamide (25 g, 0.096 mol) in 10% NaOH solution (200 ml) is stirred at 80° C. for 20 min. The reaction mixture is cooled and the solvent is removed under vacuum. The residue is acidified with 2M HCl to pH=1 and then basified with ammonium hydroxide. The solid precipitated is collected by filtration and dried under suction affording N-Pyrazin-2-ylthiourea as a solid (12 g; 80%). 1H NMR (DMSO-d6, 300 MHz): δ 8.24 (br s, 2H), 8.54 (s, 1H), 9.10 (m, 1H), 9.95 (m, 1H), 10.66 (br s, 1H). M+ (ESI): 154.9. HPLC (Method B), Rt: 3.47 min (purity: 98.23%). TLC: Chloroform/methanol (9/1): Rf−0.25. Mp: 234° C.-235° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe solvent is removed under vacuum
  3. customThe solid precipitated
  4. filtrationis collected by filtration
  5. customdried under suction

Sources & evidence

ORD record
ord-f9d7516a12e64e98bd45431504c8ae12
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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