5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-1,3,4-thiadiazole-2(3H)-thione → 5-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazole-2(3H)-thione

HRID 1492988Notes

Reaction equation

HRID 1492988 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:22]2[S:26][C:25](=[S:27])[NH:24][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-]>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([C:22]2[S:26][C:25](=[S:27])[NH:24][N:23]=2)[CH:8]=[C:9]([C:18]([CH3:19])([CH3:20])[CH3:21])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 103415325-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-1,3,4-thiadiazole-2(3H)-thione

Product 1

HCID 30370185-(3,5-Di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazole-2(3H)-thioneYield 52%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Anhydrous zinc bromide (7.3 g, 0.033 mole) is added to a suspension of 5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]1,3,4-thiadiazole-2(3H)-thione (2.7 g, 0.007 mole) in methylene chloride (10 ml). After 18 hours the mixture is diluted with methylene chloride (50 ml), washed with water (20 ml), saturated aqueous NaHCO3 (20 ml), saturated aqueous NaCl (20 ml), and dried over MgSO4. Filtration and concentration gives a solid which is recrystallized from ethyl acetate/hexane to provide 1.1 g (2.1 g theor., 52%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione, mp 259.5°-260° C.

Workup

  1. washwashed with water (20 ml), saturated aqueous NaHCO3 (20 ml), saturated aqueous NaCl (20 ml)
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration
  4. customgives a solid which
  5. customis recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6192599c21e84f65a4874526a4b4eae4
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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