Hydrochloric Acid → HCID 136067190, compound

HRID 718191Notes

Reaction equation

HRID 718191 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].C([O-])(O)=O.[Na+].[CH3:12][C:13]([CH3:19])([CH3:18])[CH2:14][C:15](Cl)=O.[OH-].[Na+].Cl>O>[CH2:14]([C:15]1[NH:6][C:4](=[O:5])[NH:3][N:2]=1)[C:13]([CH3:19])([CH3:18])[CH3:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11236Semicarbazide hydrochlorideHCID 14798Sodium HydroxideHCID 815143,3-Dimethylbutanoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 136067190HCID 136067190, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Semicarbazide hydrochloride (1.50 g, 13.6 mmol) was dissolved in water (15 mL). NaHCO3 (2.40 g, 28.6 mmol) was slowly added to the solution over 30 min at RT followed by the addition of 3,3-dimethylbutyryl chloride (2 g, 14.86 mmol). The mixture was stirred at RT for 12 h followed by the addition of solid NaOH (1.08 g, 27 mmol). The reaction mixture was stirred at 100° C. for 3 h, allowed to cool to RT and stirred for an additional 12 h. The reaction mixture was neutralized by the drop-wise addition of concentrated HCl. The solids were collected by filtration, washed with water, and dried in vacuo to afford 3-neopentyl-1H-1,2,4-triazol-5(4H)-one (0.65 g, 31%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.12 (s, 1H), 11.10 (s, 1H), 2.20 (s, 2H), 0.90 (s, 9H).

Workup

  1. stirringThe reaction mixture was stirred at 100° C. for 3 h
  2. temperatureto cool to RT
  3. stirringstirred for an additional 12 h
  4. filtrationThe solids were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-98c745eb2a8a456dae343028d2afa06c
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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