5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-3H-1,2,4-triazole-3-thione → 5-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-3H-1,2,4-triazole-3-thione

HRID 466053Notes

Reaction equation

HRID 466053 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:22]2[N:26]=[N:25][C:24](=[S:27])[N:23]=2)[CH:8]=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[O:11]COCCOC)([CH3:4])[CH3:3]>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[CH3:21][C:18]([C:9]1[CH:8]=[C:7]([C:22]2[N:26]=[N:25][C:24](=[S:27])[N:23]=2)[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:19])[CH3:20]

Participants

4

Reactant 1

HCID 189498475-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-3H-1,2,4-triazole-3-thione

Product 1

HCID 1357865375-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-3H-1,2,4-triazole-3-thione

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Anhydrous zinc bromide (6.6 g, 0.0292 mole) is added to a suspension of 5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-3H-1,2,4-triazole-3-thione (2.4 g, 0.0058 mole) in methylene chloride (6.0 m). After 18 hours the mixture is diluted with methylene chloride (30 ml), washed with water (15 ml), saturated aqueous NaHCO3 (15 ml), saturated aqueous NaCl (10 ml), and dried over MgSO4. Filtration and concentration gives a solid which is recrystallized from ethyl acetate/isopropyl ether to provide 0.8 g (1.8 g theor., 44%) of product, mp >250° C.

Workup

  1. washwashed with water (15 ml), saturated aqueous NaHCO3 (15 ml), saturated aqueous NaCl (10 ml)
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration
  4. customgives a solid which
  5. customis recrystallized from ethyl acetate/isopropyl ether
  6. customto provide 0.8 g (1.8 g theor., 44%) of product, mp >250° C.

Sources & evidence

ORD record
ord-850f90ea062f4ab7b1b8918efe6895db
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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