Formaldehyde → 1-(4-Methoxybenzyl)-N-methyl-1H-tetrazol-5-amine

HRID 881906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881906
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[C:12]([NH2:13])=[N:11][N:10]=[N:9]2)=[CH:5][CH:4]=1.[CH2:16]=O.C[O-].[Na+].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([NH:13][CH3:16])=[N:11][N:10]=[N:9]2)=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 240234561-(4-methoxy-benzyl)-1H-tetrazol-5-ylamine

Produkt 1

HCID 671541201-(4-Methoxybenzyl)-N-methyl-1H-tetrazol-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Next, to a suspension of 1-(4-methoxy-benzyl)-1H-tetrazol-5-ylamine (600 mg, 2.92 mmol) in MeOH (10 mL) were added paraformaldehyde (132 mg, 4.39 mmol) and sodium methoxide (632 mg, 25 wt % in MeOH). The mixture was refluxed for 30 min until the suspension turned into a clear solution. The mixture was cooled to room temperature and sodium borohydride (332 mg, 8.77 mmol) was added portionwise. The reaction mixture was refluxed again for 15 min. After cooled to room temperature, the reaction was quenched with H2O. The mixture was diluted with EtOAc, partially concentrated, and washed with brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10% MeOH in DCM) to give [1-(4-methoxy-benzyl)-1H-tetrazol-5-yl]-methyl-amine. 1H NMR (400 MHz, CDCl3) δ 3.00 (d, 3H, J=5.3 Hz), 3.61 (bs, 1H), 3.82 (s, 3H), 5.25 (s, 2H), 6.91 (d, 2H, J=8.8 Hz), 7.16 (d, 2H, J=8.8 Hz); MS: m/z (MH+) 220.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 30 min until the suspension
  2. temperatureThe reaction mixture was refluxed again for 15 min
  3. temperatureAfter cooled to room temperature
  4. customthe reaction was quenched with H2O
  5. additionThe mixture was diluted with EtOAc
  6. concentrationpartially concentrated
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: 10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-4f07e0d949cd477386f2e970e1b55fa6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993631B2

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