3-Chloro-2,4-pentanedione → HCID 131728329, compound

HRID 1715230Notes

Reaction equation

HRID 1715230 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([NH2:10])=[S:9].[Cl:11][CH:12]([C:16](=O)[CH3:17])[C:13](=[O:15])[CH3:14]>C(O)C>[ClH:11].[CH3:17][C:16]1[N:10]=[C:8]([NH:7][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[S:9][C:12]=1[C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 743283-Chloro-2,4-pentanedioneHCID 2771013N-Pyrazinylthiourea

Product 1

HCID 131728329HCID 131728329, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-pyrazin-2-ylthiourea (5 g, 0.032 mol) in absolute ethanol (50 ml) is added 3-chloro-2,4-pentanedione (4.4 g, 0.032 mol). The mixture is refluxed for 20 h under nitrogen. The reaction mixture is cooled down to rt and the resulting precipitate is filtered, washed with ethanol (25 ml) and dried under suction to afford 1-[4-Methyl-2-(pyrazin-2-ylamino)-1,3-thiazol-5-yl]ethanone, hydrochloride salt as white-off solid (7 g; 92%). 1H NMR (DMSO-d6, 300 MHz): δ 2.47 (s, 3H), 2.57 (s, 3H), 8.21 (s, 1H), 8.41 (s, 1H), 8.48 (s, 1H), 12.2 (br s, 1H). M+ (ESI): 234.9. HPLC (Method B), Rt: 1.56 min (purity: 97.75%). TLC: Chloroform/methanol (9/1): Rf−0.25. Mp: 224° C.-229° C.

Workup

  1. temperatureThe mixture is refluxed for 20 h under nitrogen
  2. filtrationthe resulting precipitate is filtered
  3. washwashed with ethanol (25 ml)
  4. customdried under suction

Sources & evidence

ORD record
ord-89b45cec794b42758f9cba76d19cfdcb
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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