Methanesulfonic Acid → HCID 21190630, compound

HRID 1068910Notes

Reaction equation

HRID 1068910 reaction equation
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)=[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]=[CH:8][C:9]([CH:10]=[O:11])=[CH:12][CH:13]=2)=[N:4]1)([CH3:17])([CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8255IsobutyleneHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Product 1

HCID 21190630HCID 21190630, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an autoclave, 5.0 9 (28.7 mmol) of 4-(tetrazol-5-yl)-benzaldehyde (Step 35.1) in 33 ml of toluene are heated at 110° C. for 2 hours with -2.4 g of isobutene and 377 μl of methanesulfonic acid. When cold the reaction mixture is diluted with 50 ml of ethyl acetate, washed twice with sat. NaHCO3 solution, once with water and brine, dried (Na2SO4) and concentrated by evaporation. Crystallization from ethanol yields 4-(2-tert-butyl-tetrazol-5-yl)-benzaldehyde; 1H-NMR (DMSO-d6) 10.11 (s, HCO), 8.31 (d, J=8, 2H), 8.11 (d, J=8, 2H), 1.78 (s, 9H).

Workup

  1. washwashed twice with sat. NaHCO3 solution, once with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customCrystallization from ethanol

Sources & evidence

ORD record
ord-3c07422839a442d9aa5fbc2100e7dac4
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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