Hydrochloric Acid → HCID 135407154, compound

HRID 1657064Notes

Reaction equation

HRID 1657064 reaction equation
[NH2:1][NH2:2].[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])[C:10](O)=O)([CH3:6])[CH3:5].Cl.[O-:22][C:23]#[N:24].[Na+].[OH-].[Na+]>C(O)C.O>[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([C:10]2[NH:24][C:23](=[O:22])[NH:1][N:2]=2)[CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 517096Sodium CyanateHCID 86746194HCID 86746194, compound

Product 1

HCID 135407154HCID 135407154, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid hydrazine (2.8 g, 10.6 mmol) in ethanol (140 ml) and water (50 ml) is added 1N HCl (16 ml) and sodium cyanate (1.03 g, 16 mmol). The reaction mixture is stirred at room temperature for 30 minutes and at 35° C. for five minutes. The reaction mixture is cooled, evaporated, and partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer is dried (MgSO4) and evaporated. The crude product is cyclized by refluxing a solution in 1N NaOH (2-3 equiv.) for two hours. It is neutralized with 1N HCl and extracted with ethyl acetate. Pure 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (0.32 g, 10%) is separated from 3,5-di-t-butyl-4-hydrox-ybenzoic acid by flash chromatography (silica, EtOAc), mp 276°-280° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated
  3. custompartitioned between water (100 ml) and ethyl acetate (100 ml)
  4. dry with materialThe organic layer is dried (MgSO4)
  5. customevaporated
  6. extractionextracted with ethyl acetate
  7. customPure 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (0.32 g, 10%) is separated from 3,5-di-t-butyl-4-hydrox-ybenzoic acid by flash chromatography (silica, EtOAc), mp 276°-280° C.

Sources & evidence

ORD record
ord-407422ec7f0a4a3d85da3ce9f8ef05da
Source dataset
uspto-grants-1993_10
Patent number
US05256680

Reaction notes

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