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 1493001Notes

Reaction equation

HRID 1493001 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 ml). 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-ea4a2e9a61024156a6c252f54c72f5c9
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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