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

HRID 1172156Notes

Reaction equation

HRID 1172156 reaction equation
[OH-:1].[Na+].S(Cl)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=O)=O.[C:14]1([N:20]2[C:24]([SH:25])=[N:23][N:22]=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:26]1([CH3:32])C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:10][C:9]([OH:1])([CH2:11][CH2:12][CH2:6][CH2:26][CH3:32])[CH2:8][CH2:7][S:25][C:24]1[N:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:21]=[N:22][N:23]=1

Participants

6

Reactant 4

HCID 1140Toluene3×HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 1785279861-phenyltetrazole-5-thiol

Product 1

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

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

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-01baf9e6fe344c23b222759af6b58ee0
Source dataset
uspto-grants-2010_11
Patent number
US07833995B2

Reaction notes

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