Hydrochloric Acid → HCID 19935891, compound

HRID 1761560Notes

Reaction equation

HRID 1761560 reaction equation
[CH:1]1(N(C)C(=S)NN)[CH2:5][CH2:4]CC1.Cl[CH:13]([C:19]([CH3:21])=[O:20])[C:14](OCC)=O.Cl>C(O)C>[CH2:13]([C:19]([CH3:21])=[O:20])[CH3:14].[CH3:13][CH:19]([O:20][CH:5]([CH3:4])[CH3:1])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 19847577N-Cyclopentyl-N-methylhydrazinecarbothioamide

Product 1

HCID 19935891HCID 19935891, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred slurry of 8.4 g (0.049 mole) of 4-cyclopentyl-4-methyl-3-thiosemicarbazide in 50 mL of absolute ethanol was treated with 8.1 g (0.049 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 18 hr, treated with 25 mL of 2N ethanolic hydrogen chloride and heated at reflux for 2 hr. The hot solution was filtered to remove amorphous sulfur and concentrated to a red oil which gave a crude solid product when triturated with acetone. After four recrystallizations; methyl ethyl ketone/2-propyl ether (twice), acetonitrile/acetone and finally from acetonitrile, there was obtained 3.2 g of crystalline product, mp 144°-146° C., as the hydrochloride salt.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hr
  3. filtrationThe hot solution was filtered
  4. customto remove amorphous sulfur
  5. concentrationconcentrated to a red oil which
  6. customgave a crude solid product when
  7. customtriturated with acetone
  8. customAfter four recrystallizations

Sources & evidence

ORD record
ord-b0b1859ff7ea4830a6acec190f2d9e16
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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