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

HRID 1514799ノート

反応式

HRID 1514799 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 671541201-(4-Methoxybenzyl)-N-methyl-1H-tetrazol-5-amine収率 98.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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 (0.63 g). 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.

後処理

  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)

出典と根拠

ORDレコード
ord-66bf4dbdd8c5438a816908a196ac9e12
出典データセット
uspto-grants-2012_07
特許番号
US08222286B2

反応ノート

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