Hydrochloric Acid → HCID 14500690, compound

HRID 1761541Notes

Reaction equation

HRID 1761541 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12](=S)[NH:13][NH2:14])[CH3:2].[Cl:16][CH:17]([C:23]([CH3:25])=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19].Cl>C(O)C>[ClH:16].[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:23]([CH3:25])[NH:14][N:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 2731055HCID 2731055, compound

Product 1

HCID 14500690HCID 14500690, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred slurry of 9.4 g (0.05 mole) of 4-(2,6-diethylphenyl)-3-thiosemicarbazide in 75 mL of absolute ethanol was treated with 8.25 g (0.05 mole) of ethyl 2-chloroacetoacetate. The reaction mixture was stirred at ambient temperature as the color changed from white to yellow then to a greenish-white. The reaction mixture was treated with 40 mL of 2N ethanolic hydrogen chloride, heated at reflux for 1 hr then filtered hot. The filtrate upon cooling yielded a pale yellow solid, 16 g. Recrystallization from benzene/ligroin gave 15.5 g of white granular solid which was dried at 82+ C. under high vacuum for 3 hr, mp 167°-170° C. Elemental analysis and its 1H NMR spectrum indicated the product was a hydrochloride salt.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. filtrationthen filtered hot
  4. temperatureThe filtrate upon cooling
  5. customyielded a pale yellow solid, 16 g
  6. customRecrystallization from benzene/ligroin

Sources & evidence

ORD record
ord-4c3185ca59b14469bf2efb15ddb1aa5b
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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