Sodium Hydroxide → HCID 135503683, compound

HRID 1493036Notes

Reaction equation

HRID 1493036 reaction equation
C[S-].[Na+].[CH3:4][C:5]([C:8]1[CH:13]=[C:12](/[CH:14]=[CH:15]/[C:16]2[S:17][C:18]([S:21]C)=[N:19][N:20]=2)[CH:11]=[C:10]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:9]=1[OH:27])([CH3:7])[CH3:6].[OH-].[Na+]>CN(C)C=O.O>[CH3:26][C:23]([C:10]1[CH:11]=[C:12](/[CH:14]=[CH:15]/[C:16]2[S:17][C:18](=[S:21])[NH:19][N:20]=2)[CH:13]=[C:8]([C:5]([CH3:4])([CH3:6])[CH3:7])[C:9]=1[OH:27])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4378561Sodium methanethiolateHCID 135500034HCID 135500034, compound

Product 1

HCID 135503683HCID 135503683, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Sodium thiomethoxide (0.5 g, 0.007 mole) is added to a solution of (E)-2,6-bis(1,1-dimethylethyl)-4-[2-[5-(methylthio)-1,3,4-thiadiazol-2-yl]ethenyl]-phenol (1.0 g, 0.0028 mole) in dimethylformamide (10 ml). The resulting mixture is heated to 75° C. for two hours. The solution is cooled and diluted with water (20 ml). The mixture is treated with 1M NaOH (6 ml) and the aqueous solution is washed with ether (2×). The aqueous layer is made acidic by the addition of cold 6 M HCl (3 ml) and the product is then extracted with a 1:1 ethyl acetate/diethyl ether mixture (2×). The combined organic layers are washed with brine and dried over MgSO4. Filtration and concentration in vacuo, followed by recrystallization from ethyl acetate/hexane gives 0.55 g of (E)-5-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenyl]-1,3,4-thiadiazol-2-(3H)-thione. (0.98 g theor., 57%), mp 248°-249° C.

Workup

  1. temperatureThe solution is cooled
  2. washthe aqueous solution is washed with ether (2×)
  3. additionThe aqueous layer is made acidic by the addition of cold 6 M HCl (3 ml)
  4. extractionthe product is then extracted with a 1:1 ethyl acetate/diethyl ether mixture (2×)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and concentration in vacuo
  8. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-40e772783397420081988fb5587b8555
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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