Water → N-Methyl-4-benzyloxy-2-methylaniline

HRID 1010404

反応式

HRID 1010404 の反応式
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(CO)C2C=CC=C[C:20]=2N=N1.[BH4-].[Na+].O>CN(C)C=O.CO.C(OCC)(=O)C>[CH3:20][NH:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[CH3:16]

参加物

8

反応物 4

HCID 962WaterHCID 2241691H-Benzotriazole-1-methanolHCID 4311764Sodium borohydrideHCID 167730534-(Benzyloxy)-2-methylaniline

生成物 1

HCID 22936498N-Methyl-4-benzyloxy-2-methylaniline収率 62.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 4-benzyloxy-2-methylaniline (6.55 g, 30.72 mmol) in N,N-dimethylformamide (10 ml) and methanol (60 ml), 1H-benzotriazole-1-methanol (4.58 g, 30.72 mmol) was added and the mixture was stirred for 30 minutes at room temperature. N,N-Dimethylformamide (20 ml) was added for complete dissolution of the precipitated crystals, sodium borohydride (2.32 g, 61.44 mmol) was added in small portions at a time at room temperature (internal temperature increase), and the mixture was stirred for 30 minutes. Water was added to the reaction solution, extraction was performed ethyl acetate, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (4.364 g, 19.20 mmol, 62.49%) as a brown oil.

後処理

  1. additionwas added
  2. additionwas added in small portions at a time at room temperature
  3. temperature(internal temperature increase)
  4. stirringthe mixture was stirred for 30 minutes
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. custompurified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-91f8bdb10a654ebebb34ac3d7bd5ee70
出典データセット
uspto-grants-2011_07
特許番号
US07973160B2

関連ノート

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