Water → HCID 66978380, compound

HRID 1020886Notes

Reaction equation

HRID 1020886 reaction equation
[F:1][C:2](=[C:10]([F:12])[F:11])[CH2:3][CH2:4][CH:5]([OH:9])[CH2:6][CH2:7]O.[OH-].[Na+].[C:15]1([N:21]2[C:25]([SH:26])=[N:24][N:23]=[N:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2](=[C:10]([F:12])[F:11])[CH2:3][CH2:4][CH:5]([OH:9])[CH2:6][CH2:7][S:26][C:25]1[N:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:22]=[N:23][N:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 86664076HCID 86664076, compoundHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 66978380HCID 66978380, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

Compound 3 (3.87 g) was dissolved in toluene (50 mL) and a 2N aqueous solution of sodium hydroxide (50 mL), and tetrabutylammonium bromide (700 mg) and tosyl chloride chloride (4.10 g) were added thereto under ice cooling, followed by stirring for 30 min. To the reaction solution 1-phenyl-1H-tetrazole-5-thiol (4.60 g) was added, followed by stirring at 60° C. overnight. The reaction solution was poured into water and extracted with tert-butyl methyl ether. The organic layer was washed with saturated brine; dried with sodium sulfate; and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→7:3) to obtain the title compound (5.43 g) having the following physical properties:

Workup

  1. stirringby stirring at 60° C. overnight
  2. extractionextracted with tert-butyl methyl ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with sodium sulfate
  5. concentrationand concentrated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→7:3)

Sources & evidence

ORD record
ord-2afeb8267f83400b95c776a85ec25f8c
Source dataset
uspto-grants-2014_05
Patent number
US08716490B2

Reaction notes

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