Water → N'-(4-benzyloxy-2-methylphenyl)-N-(4-fluorophenyl)-N'-methylurea

HRID 1010405

반응식

HRID 1010405 반응식
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH3:17].[H-].[Na+].[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:36])OC2C=CC=CC=2)=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:1])[C:28](=[O:36])[NH:27][C:24]2[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=2)=[C:4]([CH3:17])[CH:5]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10751974Phenyl N-(4-fluorophenyl)carbamateHCID 22936498N-Methyl-4-benzyloxy-2-methylaniline

생성물 1

HCID 22936785N'-(4-benzyloxy-2-methylphenyl)-N-(4-fluorophenyl)-N'-methylurea수율 62.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

After dissolving N-methyl-4-benzyloxy-2-methylaniline (2.64 g, 11.61 mmol) in N,N-dimethylformamide (20 ml), sodium hydride (1.16 g, 29.00 mmol, 60% in oil) was added and the mixture was stirred at 85° C. for 45 minutes under a nitrogen atmosphere. Phenyl N-(4-fluorophenyl)carbamate (3.50 g, 12.76 mmol) was added and the mixture was further stirred at 85° C. for 1 hour under a nitrogen atmosphere. After cooling to room temperature, water was added to the reaction solution, extraction was performed with 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 NH silica gel and subjected to crude purification by NH silica gel column chromatography acetate-ethanol) to obtain N′-(4-benzyloxy-2-methylphenyl)-N-(4-fluorophenyl)-N′-methylurea (2.66 g) as a yellow oil. This was dissolved in methanol (50 ml), and then 10% palladium carbon (0.2 g) was added and the mixture was stirred for 2 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and then filtrate was washed with ethanol, and the solvent was distilled off under reduced pressure. The precipitated crystals were suspended in ethanol, the suspension was diluted with diethyl ether and hexane, and the crystals were filtered out, washed with hexane and dried by aspiration to obtain the title compound (0.83 g, 3.0258 mmol, 41.86%) as brown crystals.

후처리

  1. additionwas added
  2. stirringthe mixture was further stirred at 85° C. for 1 hour under a nitrogen atmosphere
  3. temperatureAfter cooling to room temperature
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. custompurification by NH silica gel column chromatography acetate-ethanol)

출처 및 근거

ORD 기록
ord-d21ccaf8ba1645f3a7d12fb6cb822d57
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973160B2

연결된 노트

불러오는 중…