Hydrochloric Acid → HCID 14500702, compound

HRID 1761545Notes

Reaction equation

HRID 1761545 reaction equation
[CH:1]1([NH:7][C:8](=S)[NH:9][NH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:12][CH:13]([C:19]([CH3:21])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>C(O)C>[ClH:12].[CH:1]1([NH:7][C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:19]([CH3:21])[NH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 722813Hydrazinecarbothioamide, N-cyclohexyl-

Product 1

HCID 14500702HCID 14500702, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 34.7 g (0.2 mole) of 4-cyclohexyl-3-thiosemicarbazide and 32.9 g (0.2 mole) of ethyl 2-chloroacetoacetate in 350 mL of absolute ethanol was stirred under nitrogen atmosphere at ambient temperature for 2 hr, treated with 100 mL of 2N ethanolic hydrogen chloride and heated at reflux for 2 hr. The hot reaction mixture was filtered to remove an amorphous solid. The product persistently crystallized in the filter. The product was recrystallized from acetone and recovered by decating off hot acetone solvent and washing the residue with cold acetone to give 27 g of large, off-white crystals, mp 178°-182° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hr
  3. filtrationThe hot reaction mixture was filtered
  4. customto remove an amorphous solid
  5. customThe product persistently crystallized in the filter
  6. customThe product was recrystallized from acetone
  7. customrecovered
  8. washwashing the residue with cold acetone
  9. customto give 27 g of large, off-white crystals, mp 178°-182° C.

Sources & evidence

ORD record
ord-fc9eb7368e2b469eb2cd728059584241
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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