Ammonium Chloride → HCID 178470224, compound

HRID 2174287Notes

Reaction equation

HRID 2174287 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([NH:8][NH2:9])=O.[NH2:10][C:11](=S)[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Cl-].[NH4+]>C(O)C.[Cl-].[Na+].O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9][N:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 2733398Ethyl thiooxamateHCID 23424176Thiazole-2-carbohydrazide

Product 1

HCID 178470224HCID 178470224, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of thiazole-2-carbohydrazide (4.2 mmol), ethyl 2-amino-2-thioxoacetate (1 equiv) and ammonium chloride (6 equiv) in ethanol (150 mL) was placed in a sealed tube and this was warmed to 110° C. and stirred at that temperature for 11 days. The reaction solution was cooled to rt and conc. Brine was added and the mixture was adjusted to pH-6 and extracted with EtOAc. The organic phases were dried over Na2SO4, filtered and conc. The crude product was purified using SiO2 chromatography and an appropriate solvent gradient (CH3CN/MeOH/CH2Cl2) to give ethyl 3-(thiazol-2-yl)-1H-1,2,4-triazole-5-carboxylate as an off-white solid (Intermediate-2, 37% yield).

Workup

  1. customwas placed in a sealed tube
  2. temperatureThe reaction solution was cooled to rt
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customconc. The crude product was purified

Sources & evidence

ORD record
ord-bbb8d014cff9407a9b8dbf23685b47cd
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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