Benzene → HCID 14500738, compound

HRID 2350887Notes

Reaction equation

HRID 2350887 reaction equation
[CH3:1][N:2]([CH3:7])[C:3](=S)[NH:4][NH2:5].[Cl:8][CH:9]([C:15]([CH3:17])=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].C1C=CC=CC=1>C(O)C>[ClH:8].[CH3:1][N:2]([CH3:7])[C:3]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:15]([CH3:17])[NH:5][N:4]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 11858Ethyl 2-chloroacetoacetateHCID 27337004,4-Dimethyl-3-thiosemicarbazide

Product 1

HCID 14500738HCID 14500738, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred slurry of 2.5 g (0.013 mole) of 4,4-dimethyl-3-thiosemicarbazide in 50 mL of absolute ethanol was treated with 2.1 g (0.013 mole) of ethyl 2-chloroacetoacetate added at a rapid rate under nitrogen atmosphere. The reaction mixture turned yellow immediately, cleared, became cloudy and finally became a clear orange solution within 5 minutes. The reaction mixture was stirred at ambient temperature for ~72 hr, heated to reflux, filtered hot, and concentrated in vacuo to give a yellow oil which solidified. Trituration with benzene gave 3 g of tan solid. After 3 recrystallizations from benzene, 1.8 g of fine pale beige crystalline product was obtained, mp 135°-139° C. After drying at 98° C. under reduced pressure for 3 hr, mp 137-139° C. Analysis: Calculated for C9H16ClN3O2 : C, 46.26; H, 6.90; N, 17.98. Found: C, 46.05; H, 6.91; N, 18.09.

Workup

  1. additionadded at a rapid rate under nitrogen atmosphere
  2. customwithin 5 minutes
  3. temperatureheated
  4. temperatureto reflux
  5. filtrationfiltered hot
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil which

Sources & evidence

ORD record
ord-cc498ddfded042979d242111a8b0dad6
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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