Water → HCID 19773924, compound

HRID 1613529Notes

Reaction equation

HRID 1613529 reaction equation
[CH2:1]([O:7][C:8]1[CH:35]=[CH:34][C:11]([NH:12][C:13](=[S:33])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][CH:22]([C:29]([F:32])([F:31])[F:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+].O>CO.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[F:31][C:29]([F:32])([F:30])[CH:22]([O:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[S:33][C:10]3[CH:9]=[C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:35]=[CH:34][C:11]=3[N:12]=2)=[CH:15][CH:16]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19773925HCID 19773925, compound

Product 1

HCID 19773924HCID 19773924, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 887MethanolSolvent

Procedure

1.0 g (1.96 mM) of optically active 4'- hexyloxy-4-(1-trifluoromethylheptyloxymethyl)thiobenzanilide and 1.70 g (3.9 mM) of 90%-sodium hydroxide were dissolved in 15 ml of methanol. To the solution, 5 ml of an aqueous solution of 1.61 g (4.9 mM) of potassium ferricyanide was added dropwise, followed by stirring for 1 hour at room temperature. After the reaction, water was added to the reaction mixture, followed by filtration to obtain a crude crystal. The crude crystal was purified by silica gel column chromatography (eluent: toluene/hexane=1/2) and recrystallized two times from ethanol to obtain 0.49 g (0.97 mM) of optically active 2-[4-(1-trifluoromethylheptyloxymethyl)phenyl]-6-hexyloxybenzothiazole (Yield: 49%, m.p.=69.1° C.).

Workup

  1. additionwas added to the reaction mixture
  2. filtrationfollowed by filtration
  3. customto obtain a crude crystal
  4. customThe crude crystal was purified by silica gel column chromatography (eluent: toluene/hexane=1/2)
  5. customrecrystallized two times from ethanol

Sources & evidence

ORD record
ord-78ef99508c064a79a13b40bde7b3fb47
Source dataset
uspto-grants-1993_03
Patent number
US05194177

Reaction notes

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