Ethyl Acetoacetate → HCID 178445573, compound

HRID 1034124Notes

Reaction equation

HRID 1034124 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([S:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[NH:4][N:3]=1.[C:20](OCC)(=[O:25])[CH2:21][C:22]([CH3:24])=O>C(O)(=O)C>[CH2:14]([S:13][CH2:12][CH2:11][S:10][CH2:9][CH2:8][S:7][C:5]1[N:6]=[C:2]2[N:3]([N:4]=1)[C:20]([OH:25])=[CH:21][C:22]([CH3:24])=[N:1]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 1784455743-Amino-5-{2-[2-(hexylthio)ethylthio]ethylthio}-1,2,4-triazole

Product 1

HCID 178445573HCID 178445573, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of Compound 12 (3.90 g, 13.3 mmole), ethyl acetoacetate (1.94 g, 14.9 mmole), and acetic acid (8.2 mL) was heated at reflux in a dry nitrogen atmosphere overnight. On cooling, the mixture solidified. The solid was collected, washed with cold ethanol and recrystallized from ethanol to yield Compound 20 (4.03 g, 74% yield), m.p. 119°-121° C. Analysis: Calculated for C10H26N4OS3 : C, 49.71; H, 6.78; N, 14.49. Found: C, 48.98; H, 6.76; N, 14.34.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in a dry nitrogen atmosphere overnight
  3. temperatureOn cooling
  4. customThe solid was collected
  5. washwashed with cold ethanol
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a7b8f133b8c34c2f987774a843e3f9fe
Source dataset
uspto-grants-1994_05
Patent number
US05314790

Reaction notes

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