Ethyl 2-chloroacetoacetate → HCID 14500709, compound

HRID 2350890Notes

Reaction equation

HRID 2350890 reaction equation
[CH:1]1([NH:8][C:9](=S)[NH:10][NH2:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:13][CH:14]([C:20]([CH3:22])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1>[ClH:13].[CH:1]1([NH:8][C:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:22])[NH:11][N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 19847532HCID 19847532, compound

Product 1

HCID 14500709HCID 14500709, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11.6 g (0.0619 mole) of 4-cycloheptyl-3-thiosemicarbazide in 100 mL of tetrahydrofuran was stirred under nitrogen atmosphere while 10.2 g (0.062 mole) of ethyl 2-chloroacetoacetate was added. The reaction mixture quickly turned yellow and slowly became exothermic to boiling. The reaction mixture was refluxed for 1.5 hr, filtered (to remove amorphous sulfur), and concentrated in vacuo to give a yellow granular solid, 19.7 g. Several attempts at recrystallization of the material from various solvents resulted in 4 fractions all having melting points in the range of 157°-160° C. These were combined (12 g) and recrystallized from methyl isobutyl ketone, after treating with charcoal, to give 10.3 g of product. After drying at 82° C. under vacuum for 15 hr the weight was reduced to 9.8 g with mp 155°-161° C.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 1.5 hr
  3. filtrationfiltered
  4. custom(to remove amorphous sulfur)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow granular solid, 19.7 g
  7. customSeveral attempts at recrystallization of the material from various solvents
  8. customresulted in 4 fractions all having melting points in the range of 157°-160° C
  9. customrecrystallized from methyl isobutyl ketone
  10. additionafter treating with charcoal

Sources & evidence

ORD record
ord-dcc61e426a434b679cd17dd19da8c8d7
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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