Hydrochloric Acid → HCID 14500722, compound

HRID 2350896Notes

Reaction equation

HRID 2350896 reaction equation
[CH:1]1([NH:9][C:10](=S)[NH:11][NH2:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:14][CH:15]([C:21]([CH3:23])=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>C(O)C>[ClH:14].[CH:1]1([NH:9][C:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:21]([CH3:23])[NH:12][N:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 19847529N-Cyclooctylhydrazinecarbothioamide

Product 1

HCID 14500722HCID 14500722, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred slurry of 18.7 g (0.093 mole) of 4-cyclooctyl-3-thiosemicarbazide in 150 mL of absolute ethanol under nitrogen atmosphere was treated with 16.5 g (0.1 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 1.5 hr, treated with 50 mL of 2N ethanolic hydrogen chloride and heated at reflux for ~16 hr. The yellow-brown reaction mixture was filtered and concentrated in vacuo to a dark oil which solidified. Trituration of the crude product with warm acetone removed most of the color to give 17.9 g of product. Recrystallization from methyl ethyl ketone/isopropyl ether followed by recrystallization from methyl ethyl ketone gave 7.1 g of crystalline product, mp 161°-166° C. which was dried at 82° C. under reduced pressure for 3 hr (mp, 168°-171° C.).

Workup

  1. temperatureheated
  2. temperatureat reflux for ~16 hr
  3. filtrationThe yellow-brown reaction mixture was filtered
  4. concentrationconcentrated in vacuo to a dark oil which
  5. customTrituration of the crude product with warm acetone removed most of the color

Sources & evidence

ORD record
ord-4513711e955f451fa5c63e97e16d95fb
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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