Hydrochloric Acid → HCID 135407154, compound

HRID 466050Notes

Reaction equation

HRID 466050 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-hydroxybenzoic 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-hydroxybenzoic acid by flash chromatography (silica, EtOAc), mp 276°-280° C.

Sources & evidence

ORD record
ord-a901ae2d464a4673a2883d511b18c3a3
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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