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

HRID 388017

반응식

HRID 388017 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 22936498N-Methyl-4-benzyloxy-2-methylaniline수율 62.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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 saline 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.

후처리

  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 saline
  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)

출처 및 근거

ORD 기록
ord-868b6d69f9df4049ab99b8686cccfd50
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372981B2

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