Sodium hydride → 1-(2-Methyl-3-triisopropylsilanylsulfanylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one

HRID 628501Notes

Reaction equation

HRID 628501 reaction equation
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:14][C:15]1[C:20](Br)=[CH:19][CH:18]=[CH:17][C:16]=1[N:22]1[C:26](=[O:27])[N:25]([CH3:28])[N:24]=[N:23]1>O>[CH3:14][C:15]1[C:20]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])=[CH:19][CH:18]=[CH:17][C:16]=1[N:22]1[C:26](=[O:27])[N:25]([CH3:28])[N:24]=[N:23]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 898758451-(2-Methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

Product 1

HCID 898812171-(2-Methyl-3-triisopropylsilanylsulfanylphenyl)-4-methyl-1,4-dihydrotetrazole-5-oneYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Under ice-cooling, to a mixture of triisopropylsilanethiol 4.99 g and tolune 30 ml was added 60% sodium hydride 0.63 g, and the resulting mixture was stirred for thirty minutes. To the reaction mixture was added 1-(2-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 10) 2.82 g and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct 0.856 g. The reaction mixture was heated to 90° C. and was stirred for four hours. After cooling the reaction mixture, thereto was added water and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-methyl-3-triisopropylsilanylsulfanylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 3.64 g.

Workup

  1. stirringwas stirred for four hours
  2. temperatureAfter cooling the reaction mixture
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated saline
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb97a863f9a846ceb5eaa30323070832
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…