Methanesulfonic Acid → HCID 21190634, compound

HRID 1068922Notes

Reaction equation

HRID 1068922 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=[O:10])=[N:4][N:3]=[N:2]1.[CH2:14]=[C:15]([CH3:17])[CH3:16].CS(O)(=O)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:15]([N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=[O:10])=[N:4]1)([CH3:17])([CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8255IsobutyleneHCID 178519552HCID 178519552, compound

Product 1

HCID 21190634HCID 21190634, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an autoclave, 3.2 g (18.4 mmol) of 3-(tetrazol-5-yl)-benzaldehyde (see Step 59.1) in 22 ml of toluene are heated at 110° C. for 1.5 hours with ≈1.5 g of isobutene and 0.216 ml of methanesulfonic acid. When cold the reaction mixture is diluted with 200 ml of ethyl acetate, washed four times with water and once with brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/ethyl acetate=3:1) and crystallization from diethyl ether/hexane (−15° C.) yield 3-(2-tert-butyl-tetrazol-5-yl)-benzaldehyde; TLC: Rf=0.41 (hexane/ethyl acetate=3:1); FAB-MS: (M+H)+=231.

Workup

  1. washwashed four times with water
  2. dry with materialonce with brine, dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customColumn chromatography (SiO2; hexane/ethyl acetate=3:1) and crystallization from diethyl ether/hexane (−15° C.)

Sources & evidence

ORD record
ord-5027f015fd4c42ae9bc306d7ebff5a23
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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