1-Chlorobutane-2,3-dione → HCID 50998257, compound

HRID 32803Notes

Reaction equation

HRID 32803 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[Cl:5][CH2:6][C:7](=O)[C:8](=[O:10])[CH3:9]>C(O)C>[ClH:5].[NH2:1][C:2]1[S:3][CH:6]=[C:7]([C:8](=[O:10])[CH3:9])[N:4]=1

Participants

4

Reactant 2

HCID 796801-Chlorobutane-2,3-dioneHCID 2723790Thiourea

Product 1

HCID 50998257HCID 50998257, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of thiourea (8.87 g, 115 mmol) in ethanol (20.9 mL) was added 1-chloro-2,3-butanedione (13.90 g, 115 mmol) dropwise, a slight exothermic reaction resulted. The mixture was stirred at ambient temperature for 1 hour. The reaction mixture was filtered and the precipitate washed with ethyl ether (2×). The tan solid was air dried then dried under high vacuum overnight to give 1-(2-amino-thiazol-4-yl)-ethanone hydrochloride as a tan solid (21.5 g, 97%).

Workup

  1. customa slight exothermic reaction
  2. customresulted
  3. filtrationThe reaction mixture was filtered
  4. washthe precipitate washed with ethyl ether (2×)
  5. customdried
  6. customthen dried under high vacuum overnight

Sources & evidence

ORD record
ord-da76e0bc3a784691b80be3bb8de2356d
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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