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

HRID 881906노트

반응식

HRID 881906 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4f07e0d949cd477386f2e970e1b55fa6
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993631B2

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