Dimethylformamide → HCID 22909643, compound

HRID 1379091Notes

Reaction equation

HRID 1379091 reaction equation
[K].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([SH:13])=[N:10][N:9]=1.Br[C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18](O)=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=1.CN(C=[O:34])C>O>[C:21]([C:19]1[CH:20]=[C:15]([OH:34])[CH:16]=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:18]=1[S:13][C:11]1[O:12][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)=[N:9][N:10]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 708294-Bromo-2,6-di-tert-butylphenolHCID 178527948HCID 178527948, compound

Product 1

HCID 22909643HCID 22909643, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a stirring heterogeneous mixture of 5-(2-pyridyl)-1,3,4-oxadiazole-2-thiol potassium salt (2.17 g, 0.19 mol) in DMF (25 ml) under an N2 atmosphere, was added 2.85 g (0.01 mol) of 4-bromo-2,6-ditertbutylphenol. The mixture was stirred for 24 h at 110° C. After cooling, the slurry was diluted with water (100 ml) and extracted with Et2O (4×35 ml). The Et2O extracts were combined and washed with water (2×50 ml) and saturated NaCl solution (50 ml) and then dried (MgSO4). The solvent was removed in vacuo to give a solid. Chromatography on silica gel using 1/4 ethyl acetate/hexanes gave 2-(2,6-ditertbutyl-4-hydroxyphenyl)thio-5-(2-pyridyl)-1,3,4-oxadiazole (45) as a white solid (1.5 g, 40% yield; mp 128°-129° C.).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with Et2O (4×35 ml)
  3. washwashed with water (2×50 ml) and saturated NaCl solution (50 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto give a solid

Sources & evidence

ORD record
ord-f1ae37f4b8ed4c6db2afcc67dfde7d65
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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