Sodium Bicarbonate → 2,4-Dimethyl-5-(naphthalen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

HRID 867508Notes

Reaction equation

HRID 867508 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][N:14]([CH3:19])[C:15]([NH:17][CH3:18])=[S:16])=O.C([O-])(O)=O.[Na+]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[N:17]([CH3:18])[C:15](=[S:16])[N:14]([CH3:19])[N:13]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 14257821HCID 14257821, compound

Product 1

HCID 142578222,4-Dimethyl-5-(naphthalen-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

Procedure

1-(2-Naphthoyl)-2,4-dimethyl-thiosemicarbazide (5.47 g, 2.00×10-2 mole) from Example 2 and 1 molar aqueous NaHCO3 (200 ml, 2.00×10-1 mole) were stirred and warmed to reflux. After refluxing for 17 hours the reaction was allowed to cool to room temperature. The precipitate was collected by filtration, water-washed, and dried by suction. The product was crystallized from isopropyl alcohol to yield off-white, matted needles: 3.9 g (76%) mp. 173°-175° C.

Workup

  1. temperaturewarmed to reflux
  2. temperatureAfter refluxing for 17 hours the reaction
  3. filtrationThe precipitate was collected by filtration, water-
  4. washwashed
  5. customdried by suction
  6. customThe product was crystallized from isopropyl alcohol
  7. customto yield off-white

Sources & evidence

ORD record
ord-6c24a57698fa47879fae68b052f00a78
Source dataset
uspto-grants-1988_10
Patent number
US04775689

Reaction notes

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