4-Toluenesulfonyl chloride → 3-methyl-1-[(1-phenyl-1H-tetrazol-5-yl)thio]octan-3-ol

HRID 1888306Notes

Reaction equation

HRID 1888306 reaction equation
[CH3:1][C:2]([OH:11])([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4]O.[OH-].[Na+].S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[C:25]1([N:31]2[C:35]([SH:36])=[N:34][N:33]=[N:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]([OH:11])([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][S:36][C:35]1[N:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:32]=[N:33][N:34]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 231481413-Methyl-1,3-octandiolHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 231480183-methyl-1-[(1-phenyl-1H-tetrazol-5-yl)thio]octan-3-olYield 87.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent3×

Procedure

To a solution of the compound 38 (8.05 g) in toluene (98 mL) were added tetrabutylammonium bromide (1.62 g) and 2N sodium hydroxide (98 mL) at 0° C. and was added dropwise a suspension of tosyl chloride (10.5 g) in toluene (40 mL). The solution temperature was risen to room temperature and the solution was stirred for 1 Hour. A solution of 1-phenyl-1H-tetrazole-5-thiol (10.74 g) in toluene was added thereto and the solution was stirred at 60° C. for 3.5 Hours. The reaction solution was extracted with tert-butoxymethyl. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by Yamazen Parallel Prep (Brand name; column: 3 L, inject column: 2 L, n-hexane:ethyl acetate=81:19) to give the title compound (14.15 g) having the following physical data.

Workup

  1. additionwas added dropwise
  2. customwas risen to room temperature
  3. stirringthe solution was stirred at 60° C. for 3.5 Hours
  4. extractionThe reaction solution was extracted with tert-butoxymethyl
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe obtained residue was purified by Yamazen Parallel Prep (Brand name; column: 3 L, inject column: 2 L, n-hexane:ethyl acetate=81:19)

Sources & evidence

ORD record
ord-59e81f989fef407296be889ac0b1d319
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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