Hydrochloric Acid → HCID 131716142, compound

HRID 2350900Notes

Reaction equation

HRID 2350900 reaction equation
C1([N:6](C)[C:7](=S)[NH:8][NH2:9])CCCC1.[Cl:12][CH:13]([C:19]([CH3:21])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl.[CH2:23](O)[CH3:24]>>[ClH:12].[CH:24]1([CH2:23][NH:6][C:7]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:19]([CH3:21])[NH:9][N:8]=2)[CH2:21][CH2:19][CH2:13][CH2:14]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11858Ethyl 2-chloroacetoacetateHCID 19847577N-Cyclopentyl-N-methylhydrazinecarbothioamide

Product 1

HCID 131716142HCID 131716142, compound

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, methyl ethyl ketone/2-propyl ether (twice), acetonitrile/acetone

Sources & evidence

ORD record
ord-9aeb605361124ff493870cb9f965604b
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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