Water → HCID 69118047, compound

HRID 889825Notes

Reaction equation

HRID 889825 reaction equation
C(O)(=O)C(O)=O.[CH2:7]([NH:11][NH2:12])[CH2:8][CH2:9][CH3:10].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH2:21][N:22]2C(=O)CS[C:23]2=[O:28])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>CO>[CH2:7]([N:11]1[C:23](=[O:28])[NH:22][CH2:21][C:20]([C:17]2[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=2)=[N:12]1)[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 162021Butylhydrazine oxalateHCID 12061653-[2-(4-Chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

Product 1

HCID 69118047HCID 69118047, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Butylhydrazine oxalate (41 g, 230 mmol) and 40 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione (161 mmol) in 2200 mL of methanol were cooled in an ice bath and treated with 30.3 g (300 mmol) of triethylamine. The reaction mixture was stirred at room temperature for 30 minutes, then refluxed overnight. The reaction mixture was cooled and 400 mL of water was added. This mixture was extracted with ethyl acetate. The organic phase was washed twice with 10% aqueous sodium hydroxide solution, then dried and stripped. The solids obtained were recrystallized from ethyl acetate/hexane to give 9.6 g of 2-n-butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. extractionThis mixture was extracted with ethyl acetate
  4. washThe organic phase was washed twice with 10% aqueous sodium hydroxide solution
  5. customdried
  6. customThe solids obtained
  7. customwere recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a8dbef27390442189699f5cceb6a732b
Source dataset
uspto-grants-2006_02
Patent number
US06995157B2

Reaction notes

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